Cosmetici naturali: ecco perché sceglierli - Apollinea
Un cosmetico si può definire naturale quando è composto, come già detto, da ingredienti di derivazione vegetale e naturale, è dermocompatibile, ...
Benzyl Alcohol,
La cosmesi naturale sostituisce, per esempio i parabeni, che servono per preservare i prodotti dalle contaminazioni di funghi e batteri, con ingredienti naturali. Tra i conservanti uno dei più usati è il <anchor>Benzyl Alcohol,</anchor> che si presenta naturalmente in alcune piante, ed estratti di piante dalle proprietà disinfettanti come il rosmarino, il timo, l’origano e i semi di pompelmo. Anche il burro di karitè ha la stessa capacità di conservazione dei prodotti cosmetici.
Benzyl alcohol - Wikipedia
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## Contents

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- (Top)

- [1Natural occurrences](#Natural_occurrences)
- [2Preparation](#Preparation)
- [3Reactions](#Reactions)
- [4Applications](#Applications)Toggle Applications subsection  - [4.1Use in health care](#Use_in_health_care)
- [5Safety](#Safety)
- [6References](#References)
- [7External links](#External_links)

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# Benzyl alcohol

38 languages

- [العربية](https://ar.wikipedia.org/wiki/%D9%83%D8%AD%D9%88%D9%84_%D8%A8%D9%86%D8%B2%D9%8A%D9%84%D9%8A "كحول بنزيلي – Arabic")
- [تۆرکجه](https://azb.wikipedia.org/wiki/%D8%A8%D9%86%D8%B2%DB%8C%D9%84_%D8%A7%D9%84%DA%A9%D9%88%D9%84 "بنزیل الکول – South Azerbaijani")
- [Беларуская](https://be.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D1%96%D0%BB%D0%B0%D0%B2%D1%8B_%D1%81%D0%BF%D1%96%D1%80%D1%82 "Бензілавы спірт – Belarusian")
- [Català](https://ca.wikipedia.org/wiki/Alcohol_benz%C3%ADlic "Alcohol benzílic – Catalan")
- [Čeština](https://cs.wikipedia.org/wiki/Benzylalkohol "Benzylalkohol – Czech")
- [Dansk](https://da.wikipedia.org/wiki/Benzylalkohol "Benzylalkohol – Danish")
- [Deutsch](https://de.wikipedia.org/wiki/Benzylalkohol "Benzylalkohol – German")
- [Eesti](https://et.wikipedia.org/wiki/Bens%C3%BC%C3%BClalkohol "Bensüülalkohol – Estonian")
- [Ελληνικά](https://el.wikipedia.org/wiki/%CE%92%CE%B5%CE%BD%CE%B6%CF%85%CE%BB%CE%B9%CE%BA%CE%AE_%CE%B1%CE%BB%CE%BA%CE%BF%CF%8C%CE%BB%CE%B7 "Βενζυλική αλκοόλη – Greek")
- [Español](https://es.wikipedia.org/wiki/Alcohol_benc%C3%ADlico "Alcohol bencílico – Spanish")
- [Esperanto](https://eo.wikipedia.org/wiki/Benzila_alkoholo "Benzila alkoholo – Esperanto")
- [Euskara](https://eu.wikipedia.org/wiki/Alkohol_bentziliko "Alkohol bentziliko – Basque")
- [فارسی](https://fa.wikipedia.org/wiki/%D8%A8%D9%86%D8%B2%DB%8C%D9%84_%D8%A7%D9%84%DA%A9%D9%84 "بنزیل الکل – Persian")
- [Français](https://fr.wikipedia.org/wiki/Alcool_benzylique "Alcool benzylique – French")
- [한국어](https://ko.wikipedia.org/wiki/%EB%B2%A4%EC%A7%88_%EC%95%8C%EC%BD%94%EC%98%AC "벤질 알코올 – Korean")
- [Հայերեն](https://hy.wikipedia.org/wiki/%D4%B2%D5%A5%D5%B6%D5%A6%D5%AB%D5%AC_%D5%BD%D5%BA%D5%AB%D6%80%D5%BF "Բենզիլ սպիրտ – Armenian")
- [हिन्दी](https://hi.wikipedia.org/wiki/%E0%A4%AC%E0%A5%87%E0%A4%A8%E0%A5%8D%E0%A4%9C%E0%A4%BE%E0%A4%87%E0%A4%B2_%E0%A4%85%E0%A4%B2%E0%A5%8D%E0%A4%95%E0%A5%8B%E0%A4%B9%E0%A4%B2 "बेन्जाइल अल्कोहल – Hindi")
- [Italiano](https://it.wikipedia.org/wiki/Alcol_benzilico "Alcol benzilico – Italian")
- [עברית](https://he.wikipedia.org/wiki/%D7%91%D7%A0%D7%96%D7%99%D7%9C_%D7%90%D7%9C%D7%9B%D7%95%D7%94%D7%95%D7%9C "בנזיל אלכוהול – Hebrew")
- [ქართული](https://ka.wikipedia.org/wiki/%E1%83%91%E1%83%94%E1%83%9C%E1%83%96%E1%83%98%E1%83%9A%E1%83%98%E1%83%A1_%E1%83%A1%E1%83%9E%E1%83%98%E1%83%A0%E1%83%A2%E1%83%98 "ბენზილის სპირტი – Georgian")
- [Magyar](https://hu.wikipedia.org/wiki/Benzil-alkohol "Benzil-alkohol – Hungarian")
- [Македонски](https://mk.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%B8%D0%BB_%D0%B0%D0%BB%D0%BA%D0%BE%D1%85%D0%BE%D0%BB "Бензил алкохол – Macedonian")
- [Nederlands](https://nl.wikipedia.org/wiki/Benzylalcohol "Benzylalcohol – Dutch")
- [日本語](https://ja.wikipedia.org/wiki/%E3%83%99%E3%83%B3%E3%82%B8%E3%83%AB%E3%82%A2%E3%83%AB%E3%82%B3%E3%83%BC%E3%83%AB "ベンジルアルコール – Japanese")
- [Oʻzbekcha / ўзбекча](https://uz.wikipedia.org/wiki/Benzil_spirt "Benzil spirt – Uzbek")
- [Polski](https://pl.wikipedia.org/wiki/Alkohol_benzylowy "Alkohol benzylowy – Polish")
- [Português](https://pt.wikipedia.org/wiki/%C3%81lcool_benz%C3%ADlico "Álcool benzílico – Portuguese")
- [Română](https://ro.wikipedia.org/wiki/Alcool_benzilic "Alcool benzilic – Romanian")
- [Русский](https://ru.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%B8%D0%BB%D0%BE%D0%B2%D1%8B%D0%B9_%D1%81%D0%BF%D0%B8%D1%80%D1%82 "Бензиловый спирт – Russian")
- [Slovenčina](https://sk.wikipedia.org/wiki/Benzylalkohol "Benzylalkohol – Slovak")
- [Српски / srpski](https://sr.wikipedia.org/wiki/Benzil_alkohol "Benzil alkohol – Serbian")
- [Srpskohrvatski / српскохрватски](https://sh.wikipedia.org/wiki/Benzil_alkohol "Benzil alkohol – Serbo-Croatian")
- [Suomi](https://fi.wikipedia.org/wiki/Bentsyylialkoholi "Bentsyylialkoholi – Finnish")
- [Svenska](https://sv.wikipedia.org/wiki/Bensylalkohol "Bensylalkohol – Swedish")
- [தமிழ்](https://ta.wikipedia.org/wiki/%E0%AE%AA%E0%AF%86%E0%AE%A9%E0%AF%8D%E0%AE%9A%E0%AF%88%E0%AE%B2%E0%AF%8D_%E0%AE%86%E0%AE%B2%E0%AF%8D%E0%AE%95%E0%AE%95%E0%AE%BE%E0%AE%B2%E0%AF%8D "பென்சைல் ஆல்ககால் – Tamil")
- [Türkçe](https://tr.wikipedia.org/wiki/Benzil_alkol "Benzil alkol – Turkish")
- [Українська](https://uk.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%B8%D0%BB%D0%BE%D0%B2%D0%B8%D0%B9_%D1%81%D0%BF%D0%B8%D1%80%D1%82 "Бензиловий спирт – Ukrainian")
- [中文](https://zh.wikipedia.org/wiki/%E8%8B%AF%E7%94%B2%E9%86%87 "苯甲醇 – Chinese")

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From Wikipedia, the free encyclopedia

Aromatic alcohol

Not to be confused with [benzoic acid](/wiki/Benzoic_acid "Benzoic acid"), [cresol](/wiki/Cresol "Cresol"), or [phenol](/wiki/Phenol "Phenol").

Benzyl alcohol
[![Benzyl alcohol](//upload.wikimedia.org/wikipedia/commons/thumb/f/fb/Alkohol_benzylowy.svg/150px-Alkohol_benzylowy.svg.png)](/wiki/File:Alkohol_benzylowy.svg "Benzyl alcohol")[![Benzyl alcohol](//upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Benzyl-alcohol-3D-vdW.png/100px-Benzyl-alcohol-3D-vdW.png)](/wiki/File:Benzyl-alcohol-3D-vdW.png "Benzyl alcohol")Names
[Preferred IUPAC name](/wiki/Preferred_IUPAC_name "Preferred IUPAC name")

Phenylmethanol

(Hydroxymethyl)benzene

Other names

Benzyl alcohol

α-Cresol

α-Toluenol

α-Hydroxytoluene

alpha-Hydroxyphenylmethane

Phenylcarbinol

Benzenemethanol

Benzyl hydroxide

Benzylic acid

Identifiers

[CAS Number](/wiki/CAS_Registry_Number "CAS Registry Number")

- [100-51-6](https://commonchemistry.cas.org/detail?cas_rn=100-51-6)![check](//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png)Y

3D model ( [JSmol](/wiki/JSmol "JSmol"))

- [Interactive image](https://chemapps.stolaf.edu/jmol/jmol.php?model=c1ccc%28cc1%29CO)
- [Interactive image](https://chemapps.stolaf.edu/jmol/jmol.php?model=c1ccc%28cc1%29CO)

[ChEBI](/wiki/ChEBI "ChEBI")

- [CHEBI:17987](https://www.ebi.ac.uk/chebi/searchId.do?chebiId=17987)![check](//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png)Y

[ChEMBL](/wiki/ChEMBL "ChEMBL")

- [ChEMBL720](https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL720)![check](//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png)Y

[ChemSpider](/wiki/ChemSpider "ChemSpider")

- [13860335](https://www.chemspider.com/Chemical-Structure.13860335.html)![check](//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png)Y

[ECHA InfoCard](/wiki/ECHA_InfoCard "ECHA InfoCard")[100.002.600](https://echa.europa.eu/substance-information/-/substanceinfo/100.002.600)[![Edit this at Wikidata](//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png)](https://www.wikidata.org/wiki/Q52353#P2566 "Edit this at Wikidata")[EC Number](/wiki/European_Community_number "European Community number")

- 202-859-9

[E number](/wiki/E_number "E number")E1519 [(additional chemicals)](/wiki/E_number#E1000–E1599 "E number")[KEGG](/wiki/KEGG "KEGG")

- [D00077](https://www.kegg.jp/entry/D00077)![check](//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png)Y

[PubChem](/wiki/PubChem "PubChem") CID

- [244](https://pubchem.ncbi.nlm.nih.gov/compound/244)

[RTECS number](/wiki/RTECS "RTECS")

- DN3150000

[UNII](/wiki/Unique_Ingredient_Identifier "Unique Ingredient Identifier")

- [LKG8494WBH](https://precision.fda.gov/uniisearch/srs/unii/LKG8494WBH)![check](//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png)Y

[CompTox Dashboard](/wiki/CompTox_Chemicals_Dashboard "CompTox Chemicals Dashboard")(EPA)

- [DTXSID5020152](https://comptox.epa.gov/dashboard/chemical/details/DTXSID5020152)[![Edit this at Wikidata](//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png)](https://www.wikidata.org/wiki/Q52353#P3117 "Edit this at Wikidata")

[InChI](/wiki/International_Chemical_Identifier "International Chemical Identifier")

- InChI=1S/C7H8O/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2![check](//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png)Y



Key: WVDDGKGOMKODPV-UHFFFAOYSA-N![check](//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png)Y

- InChI=1/C7H8O/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2



Key: WVDDGKGOMKODPV-UHFFFAOYAH


[SMILES](/wiki/Simplified_molecular-input_line-entry_system "Simplified molecular-input line-entry system")

- c1ccc(cc1)CO

- c1ccc(cc1)CO


Properties[\[1\]](#cite_note-1)

[Chemical formula](/wiki/Chemical_formula "Chemical formula")

C7H8O[Molar mass](/wiki/Molar_mass "Molar mass")108.140 g·mol−1Appearance
Colorless liquid
[Odor](/wiki/Odor "Odor")Slightly aromatic
[Density](/wiki/Density "Density")1.044 g/cm3[Melting point](/wiki/Melting_point "Melting point")−15.2 °C (4.6 °F; 257.9 K)
[Boiling point](/wiki/Boiling_point "Boiling point")205.3 °C (401.5 °F; 478.4 K)

[Solubility in water](/wiki/Aqueous_solution "Aqueous solution")

3.50 g/100 mL (20 °C)

4.29 g/100 mL (25 °C)
[Solubility](/wiki/Solubility "Solubility") in other solvents
Miscible with [benzene](/wiki/Benzene "Benzene"), [methanol](/wiki/Methanol "Methanol"), [chloroform](/wiki/Chloroform "Chloroform"), [ethanol](/wiki/Ethanol "Ethanol"), [ether](/wiki/Diethyl_ether "Diethyl ether"), [acetone](/wiki/Acetone "Acetone")[log _P_](/wiki/Partition_coefficient "Partition coefficient")1.10
[Vapor pressure](/wiki/Vapor_pressure "Vapor pressure")0.18 kPa (60 °C)
[Acidity](/wiki/Acid_dissociation_constant "Acid dissociation constant") (p _K_ a)
15.40

[Magnetic susceptibility](/wiki/Magnetic_susceptibility "Magnetic susceptibility") (χ)

−71.83·10−6 cm3/mol

[Refractive index](/wiki/Refractive_index "Refractive index") ( _n_ D)

1.5396
[Viscosity](/wiki/Viscosity "Viscosity")5.474 cP

[Dipole moment](/wiki/Dipole#Molecular_dipoles "Dipole")

1.67 D
Thermochemistry

[Std molar\
\
entropy](/wiki/Standard_molar_entropy "Standard molar entropy")( _S_ ⦵298)

217.8 J/(K·mol)

[Std enthalpy of\
\
formation](/wiki/Standard_enthalpy_change_of_formation "Standard enthalpy change of formation")(Δf _H_ ⦵298)

−352 kJ/mol
Hazards
[**NFPA 704**](/wiki/NFPA_704 "NFPA 704") (fire diamond)

![NFPA 704 four-colored diamond](//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png)

[1](/wiki/NFPA_704#Blue "NFPA 704")

[1](/wiki/NFPA_704#Red "NFPA 704")

[0](/wiki/NFPA_704#Yellow "NFPA 704")

[Flash point](/wiki/Flash_point "Flash point")93 °C (199 °F; 366 K)

[Autoignition\
\
temperature](/wiki/Autoignition_temperature "Autoignition temperature")

436 °C (817 °F; 709 K)
[Explosive limits](/wiki/Explosive_limit "Explosive limit")1.3–13%
**Lethal dose** or concentration (LD, LC):

LD50 ( [median dose](/wiki/Lethal_dose#LD50 "Lethal dose"))

1250 mg/kg (rat, oral)
[Safety data sheet](/wiki/Safety_data_sheet "Safety data sheet") (SDS)
[External MSDS](http://hazard.com/msds/mf/baker/baker/files/b1885.htm)Pharmacology

[ATC code](/wiki/Anatomical_Therapeutic_Chemical_Classification_System "Anatomical Therapeutic Chemical Classification System")

[P03AX06](/wiki/ATC_code_P03 "ATC code P03") ([WHO](https://www.whocc.no/atc_ddd_index/?code=P03AX06))

Except where otherwise noted, data are given for materials in their [standard state](/wiki/Standard_state "Standard state") (at 25 °C \[77 °F\], 100 kPa).

![☒](//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png)N[verify](https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=443418046&page2=Benzyl+alcohol) ( [what is](/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation "Wikipedia:WikiProject Chemicals/Chembox validation") ![check](//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png)Y![☒](//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png)N ?)

[Infobox references](/wiki/Wikipedia:Chemical_infobox#References "Wikipedia:Chemical infobox")

Chemical compound

**Benzyl alcohol** (also known as **α- [cresol](/wiki/Cresol "Cresol")**) is an [aromatic](/wiki/Aromatic "Aromatic") [alcohol](/wiki/Alcohols "Alcohols") with the formula C6H5CH2OH. The [benzyl](/wiki/Benzyl "Benzyl") group is often abbreviated "Bn" (not to be confused with "Bz" which is used for [benzoyl](/wiki/Benzoyl "Benzoyl")), thus benzyl alcohol is denoted as BnOH. Benzyl alcohol is a colorless liquid with a mild pleasant aromatic odor. It is useful as a solvent for its polarity, low toxicity, and low [vapor pressure](/wiki/Vapor_pressure "Vapor pressure"). Benzyl alcohol has moderate [solubility](/wiki/Solubility "Solubility") in water (4 g/100 mL) and is [miscible](/wiki/Miscibility "Miscibility") in alcohols and [diethyl ether](/wiki/Diethyl_ether "Diethyl ether"). The [anion](/wiki/Anion "Anion") produced by [deprotonation](/wiki/Deprotonation "Deprotonation") of the alcohol group is known as **benzylate** or **benzyloxide**.

## Natural occurrences

\[ [edit](/w/index.php?title=Benzyl_alcohol&action=edit&section=1 "Edit section: Natural occurrences")\]

Benzyl alcohol is produced naturally by many plants and is commonly found in fruits and teas. It is also found in a variety of [essential oils](/wiki/Essential_oil "Essential oil") including [jasmine](/wiki/Jasmine "Jasmine"), [hyacinth](/wiki/Hyacinth_(plant) "Hyacinth (plant)") and [ylang-ylang](/wiki/Ylang-ylang "Ylang-ylang").[\[2\]](#cite_note-2) It is also found in [castoreum](/wiki/Castoreum "Castoreum") from the [castor sacs](/wiki/Castor_sac "Castor sac") of beavers.[\[3\]](#cite_note-3) Benzyl esters also occur naturally.[\[4\]](#cite_note-4)

## Preparation

\[ [edit](/w/index.php?title=Benzyl_alcohol&action=edit&section=2 "Edit section: Preparation")\]

Benzyl alcohol is produced industrially from [toluene](/wiki/Toluene "Toluene") via [benzyl chloride](/wiki/Benzyl_chloride "Benzyl chloride"), which is hydrolyzed:

C6H5CH2Cl + H2O → C6H5CH2OH + HCl

Another route entails hydrogenation of [benzaldehyde](/wiki/Benzaldehyde "Benzaldehyde"), a by-product of the oxidation of toluene to [benzoic acid](/wiki/Benzoic_acid "Benzoic acid").[\[5\]](#cite_note-ull-5)

For laboratory use, [Grignard reaction](/wiki/Grignard_reaction "Grignard reaction") of [phenylmagnesium bromide](/wiki/Phenylmagnesium_bromide "Phenylmagnesium bromide") (C6H5MgBr) with [formaldehyde](/wiki/Formaldehyde "Formaldehyde") and the [Cannizzaro reaction](/wiki/Cannizzaro_reaction "Cannizzaro reaction") of benzaldehyde also give benzyl alcohol. The latter also gives benzoic acid, an example of an organic [disproportionation](/wiki/Disproportionation "Disproportionation") reaction.

## Reactions

\[ [edit](/w/index.php?title=Benzyl_alcohol&action=edit&section=3 "Edit section: Reactions")\]

Like most alcohols, it reacts with [carboxylic acids](/wiki/Carboxylic_acid "Carboxylic acid") to form [esters](/wiki/Ester "Ester"). In organic synthesis, benzyl esters are popular [protecting groups](/wiki/Protecting_group "Protecting group") because they can be removed by mild [hydrogenolysis](/wiki/Hydrogenolysis "Hydrogenolysis").[\[6\]](#cite_note-6)

Benzyl alcohol reacts with [acrylonitrile](/wiki/Acrylonitrile "Acrylonitrile") to give [_N_-benzylacrylamide](/w/index.php?title=N-Benzylacrylamide&action=edit&redlink=1 "N-Benzylacrylamide (page does not exist)"). This is an example of a [Ritter reaction](/wiki/Ritter_reaction "Ritter reaction"):[\[7\]](#cite_note-7)

C6H5CH2OH + NCCHCH2 → C6H5CH2N(H)C(O)CHCH2

## Applications

\[ [edit](/w/index.php?title=Benzyl_alcohol&action=edit&section=4 "Edit section: Applications")\]

Benzyl alcohol is used as a general [solvent](/wiki/Solvent "Solvent") for inks, waxes, shellacs, paints, [lacquers](/wiki/Lacquer "Lacquer"), and [epoxy resin](/wiki/Epoxy_resin "Epoxy resin") coatings. Thus it can be used in paint strippers, especially when combined with compatible [viscosity](/wiki/Viscosity "Viscosity") enhancers to encourage the mixture to cling to painted surfaces.[\[8\]](#cite_note-8)

It is a precursor to a variety of [esters](/wiki/Ester "Ester") and [ethers](/wiki/Diethyl_ether "Diethyl ether"), used in the soap, perfume, and [flavor industries](/wiki/Flavor_industry "Flavor industry"). E.g. [benzyl benzoate](/wiki/Benzyl_benzoate "Benzyl benzoate"), [benzyl salicylate](/wiki/Benzyl_salicylate "Benzyl salicylate"), [benzyl cinnamate](/wiki/Benzyl_cinnamate "Benzyl cinnamate"), [dibenzyl ether](/wiki/Dibenzyl_ether "Dibenzyl ether"), [benzyl butyl phthalate](/wiki/Benzyl_butyl_phthalate "Benzyl butyl phthalate").

It can be used as a local anesthetic, especially with epinephrine.[\[9\]](#cite_note-9)

As a dye solvent, it enhances the process of dying wool, nylon, and leather.[\[10\]](#cite_note-AshAsh2004-10)

### Use in health care

\[ [edit](/w/index.php?title=Benzyl_alcohol&action=edit&section=5 "Edit section: Use in health care")\]

Benzyl alcohol is used as a [bacteriostatic](/wiki/Bacteriostat "Bacteriostat") preservative at low concentration in intravenous medications, cosmetics, and topical drugs.[\[11\]](#cite_note-analsci.27.865-11) Some caution is necessary if a high percent of benzyl alcohol is used as benzaldehyde arises from benzyl alcohol when used as preservative in an injectable formulation solution.[\[11\]](#cite_note-analsci.27.865-11)[\[12\]](#cite_note-12)

Benzyl alcohol, sold under the brand name **Ulesfia**, was approved by the U.S. [Food and Drug Administration](/wiki/Food_and_Drug_Administration "Food and Drug Administration") (FDA) in 2009, as a 5% solution for the treatment of [head lice](/wiki/Head-louse_infestation "Head-louse infestation") in people 6 months of age and older.[\[13\]](#cite_note-Ulesfia_FDA_label-13) It affects the louse's [spiracles](/wiki/Spiracle_(arthropods) "Spiracle (arthropods)"), preventing them from closing.[\[13\]](#cite_note-Ulesfia_FDA_label-13) These then become clogged with water or mineral oil or other matter and cause the insect to die from [asphyxiation](/wiki/Asphyxiation "Asphyxiation").[\[13\]](#cite_note-Ulesfia_FDA_label-13)

Benzyl alcohol is used effectively for treating lice infestations as the active ingredient in lotion shampoo with 5% benzyl alcohol.[\[13\]](#cite_note-Ulesfia_FDA_label-13)

Benzyl alcohol is an ingredient used in the manufacture of soaps, topical creams, skin lotions, shampoos, and facial cleansers and is popular due to its anti-bacterial and anti-fungal properties. It is a common ingredient in a variety of household products.

## Safety

\[ [edit](/w/index.php?title=Benzyl_alcohol&action=edit&section=6 "Edit section: Safety")\]

Sensitization to benzyl alcohol occurs very rarely, mainly in patients with [stasis dermatitis](/wiki/Stasis_dermatitis "Stasis dermatitis").[\[14\]](#cite_note-14)

Benzyl alcohol is not considered to be a carcinogen, and no data are available regarding teratogenic or reproductive effects.[\[5\]](#cite_note-ull-5)

Benzyl alcohol has low acute toxicity with an [LD50](/wiki/Median_lethal_dose "Median lethal dose") of 1.2 g/kg in rats.[\[5\]](#cite_note-ull-5) It oxidizes rapidly in healthy individuals to [benzoic acid](/wiki/Benzoic_acid "Benzoic acid"), conjugated with glycine in the liver, and excreted as [hippuric acid](/wiki/Hippuric_acid "Hippuric acid"). Very high concentrations can result in toxic effects including respiratory failure, vasodilation, hypotension, convulsions, and paralysis.

Benzyl alcohol is toxic to [neonates](/wiki/Infant "Infant") and is associated with the [gasping syndrome](/wiki/Gasping_syndrome "Gasping syndrome").[\[15\]](#cite_note-pth-15)[\[16\]](#cite_note-16)

## References

\[ [edit](/w/index.php?title=Benzyl_alcohol&action=edit&section=7 "Edit section: References")\]

01. **[^](#cite_ref-1)**["Benzyl alcohol"](https://web.archive.org/web/20090726101848/http://sitem.herts.ac.uk/aeru/footprint/en/Reports/953.htm). Archived from [the original](http://sitem.herts.ac.uk/aeru/footprint/en/Reports/953.htm) on 26 July 2009.
02. **[^](#cite_ref-2)**_[The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals](/wiki/Merck_Index "Merck Index")_ (11th ed.), Merck, 1989, [ISBN](/wiki/ISBN_(identifier) "ISBN (identifier)") [091191028X](/wiki/Special:BookSources/091191028X "Special:BookSources/091191028X"), 1138
03. **[^](#cite_ref-3)**Dietland Muller-Schwarze (2003). [_The Beaver: Its Life and Impact_](https://books.google.com/books?id=HZ5WjXB5Pr8C&q=Castoreum%20beekeeping&pg=PA43). Cornell University Press. p. 43. [ISBN](/wiki/ISBN_(identifier) "ISBN (identifier)") [978-0-8014-5010-5](/wiki/Special:BookSources/978-0-8014-5010-5 "Special:BookSources/978-0-8014-5010-5").
04. **[^](#cite_ref-4)**d'Auria, John C.; Chen, Feng; Pichersky, Eran (2002). ["Characterization of an Acyltransferase Capable of Synthesizing Benzylbenzoate and Other Volatile Esters in Flowers and Damaged Leaves of Clarkia breweri"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC166578). _Plant Physiology_. **130** (1): 466–476. [doi](/wiki/Doi_(identifier) "Doi (identifier)"): [10.1104/pp.006460](https://doi.org/10.1104%2Fpp.006460). [PMC](/wiki/PMC_(identifier) "PMC (identifier)") [166578](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC166578). [PMID](/wiki/PMID_(identifier) "PMID (identifier)") [12226525](https://pubmed.ncbi.nlm.nih.gov/12226525).
05. ^ [_**a**_](#cite_ref-ull_5-0) [_**b**_](#cite_ref-ull_5-1) [_**c**_](#cite_ref-ull_5-2)Friedrich Brühne; Elaine Wright (2007). "Benzyl Alcohol". _[Ullmann's Encyclopedia of Industrial Chemistry](/wiki/Ullmann%27s_Encyclopedia_of_Industrial_Chemistry "Ullmann's Encyclopedia of Industrial Chemistry")_. Weinheim: Wiley-VCH. [doi](/wiki/Doi_(identifier) "Doi (identifier)"): [10.1002/14356007.a04\_001](https://doi.org/10.1002%2F14356007.a04_001). [ISBN](/wiki/ISBN_(identifier) "ISBN (identifier)") [978-3527306732](/wiki/Special:BookSources/978-3527306732 "Special:BookSources/978-3527306732").
06. **[^](#cite_ref-6)**Furuta, Kyoji; Gao, Qing-Zhi; Yamamoto, Hisashi (1995). ["Chiral (Acyloxy)borane Complex-Catalyzed Asymmetric Diels-Alder Reaction: (1 _R_)-1,3,4-Trimethyl-3-Cyclohexene-1-Carboxaldehyde"](http://www.orgsyn.org/demo.aspx?prep=cv9p0722). _[Organic Syntheses](/wiki/Organic_Syntheses "Organic Syntheses")_. **72**: 86; _Collected Volumes_, vol. 9, p. 722.
07. **[^](#cite_ref-7)**Parris, Chester L. (1962). [" _N_-benzylacrylamide"](http://www.orgsyn.org/demo.aspx?prep=cv5p0073). _[Organic Syntheses](/wiki/Organic_Syntheses "Organic Syntheses")_. **42**: 16; _Collected Volumes_, vol. 5, p. 73.
08. **[^](#cite_ref-8)**[_Benzyl alcohol_](https://web.archive.org/web/20090421060841/http://chemicalland21.com/industrialchem/solalc/BENZYL%20ALCOHOL.htm), chemicalland21.com, archived from [the original](http://www.chemicalland21.com/industrialchem/solalc/BENZYL%20ALCOHOL.htm) on 21 April 2009, retrieved 14 May 2006
09. **[^](#cite_ref-9)**Wilson, L.; Martin, S. (May 1999). "Benzyl alcohol as an alternative local anesthetic". _Annals of Emergency Medicine_. **33** (5): 495–499. [doi](/wiki/Doi_(identifier) "Doi (identifier)"): [10.1016/s0196-0644(99)70335-5](https://doi.org/10.1016%2Fs0196-0644%2899%2970335-5). [PMID](/wiki/PMID_(identifier) "PMID (identifier)") [10216324](https://pubmed.ncbi.nlm.nih.gov/10216324).
10. **[^](#cite_ref-AshAsh2004_10-0)**Michael Ash; Irene Ash (2004). [_Handbook of Preservatives_](https://books.google.com/books?id=XZ2QB7bu5LwC&pg=PA487). Synapse Info Resources. p. 292. [ISBN](/wiki/ISBN_(identifier) "ISBN (identifier)") [978-1-890595-66-1](/wiki/Special:BookSources/978-1-890595-66-1 "Special:BookSources/978-1-890595-66-1").
11. ^ [_**a**_](#cite_ref-analsci.27.865_11-0) [_**b**_](#cite_ref-analsci.27.865_11-1)H. A. Mashayekhi; M. Rezaee; Sh. S. Garmaroudi; N. Montazeri; S. J. Ahmadi (2011). ["Rapid and sensitive determination of benzaldehyde arising from benzyl alcohol used as preservative in an injectable formulation solution using dispersive liquid–liquid microextraction followed by gas chromatography"](https://doi.org/10.2116%2Fanalsci.27.865). _Anal. Sci_. **27** (8): 865–868. [doi](/wiki/Doi_(identifier) "Doi (identifier)"):[10.2116/analsci.27.865](https://doi.org/10.2116%2Fanalsci.27.865). [PMID](/wiki/PMID_(identifier) "PMID (identifier)") [21828928](https://pubmed.ncbi.nlm.nih.gov/21828928).
12. **[^](#cite_ref-12)**N. N. Sudareva; E. V. Chubarova (2006). "Time-dependent conversion of benzyl alcohol to benzaldehyde and benzoic acid in aqueous solutions". _J. Pharm. Biomed. Anal_. **41** (4): 1380–1385. [doi](/wiki/Doi_(identifier) "Doi (identifier)"): [10.1016/j.jpba.2006.02.028](https://doi.org/10.1016%2Fj.jpba.2006.02.028). [PMID](/wiki/PMID_(identifier) "PMID (identifier)") [16564153](https://pubmed.ncbi.nlm.nih.gov/16564153).
13. ^ [_**a**_](#cite_ref-Ulesfia_FDA_label_13-0) [_**b**_](#cite_ref-Ulesfia_FDA_label_13-1) [_**c**_](#cite_ref-Ulesfia_FDA_label_13-2) [_**d**_](#cite_ref-Ulesfia_FDA_label_13-3)["Ulesfia- benzyl alcohol lotion"](https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=5754f979-32b7-4406-a3a9-ed36aac6a37a). _DailyMed_. 8 April 2019. Retrieved 27 April 2020.
14. **[^](#cite_ref-14)**["Registration Dossier - ECHA"](https://echa.europa.eu/registration-dossier/-/registered-dossier/14748/7/5/1). _echa.europa.eu_. Retrieved 20 April 2023.
15. **[^](#cite_ref-pth_15-0)**Carl R. Baum (2008), "Examples of mass exposures involving the pediatric population", in Jerrold B. Leikin; Frank P. Paloucek (eds.), _Poisoning and Toxicology Handbook_ (4th ed.), Informa, p. 726.
16. **[^](#cite_ref-16)**Juan Gershanik; et al. (1982), "The gasping syndrome and benzyl alcohol poisoning", _[N Engl J Med](/wiki/N_Engl_J_Med "N Engl J Med")_, **307** (22): 1384–8, [doi](/wiki/Doi_(identifier) "Doi (identifier)"): [10.1056/nejm198211253072206](https://doi.org/10.1056%2Fnejm198211253072206), [PMID](/wiki/PMID_(identifier) "PMID (identifier)") [7133084](https://pubmed.ncbi.nlm.nih.gov/7133084).

## External links

\[ [edit](/w/index.php?title=Benzyl_alcohol&action=edit&section=8 "Edit section: External links")\]

- [International Chemical Safety Card 0833](https://www.ilo.org/dyn/icsc/showcard.display?p_lang=en&p_card_id=0833&p_version=2)

- [v](/wiki/Template:Alcohols "Template:Alcohols")
- [t](/wiki/Template_talk:Alcohols "Template talk:Alcohols")
- [e](/wiki/Special:EditPage/Template:Alcohols "Special:EditPage/Template:Alcohols")

[Alcohols](/wiki/Alcohol_(chemistry) "Alcohol (chemistry)")

By consumption

[Alcohols found in\
\
alcoholic drinks](/wiki/Comparison_of_psychoactive_alcohols_in_alcoholic_drinks "Comparison of psychoactive alcohols in alcoholic drinks")

- [1-Propanol](/wiki/1-Propanol "1-Propanol")
- [2-Methyl-1-butanol](/wiki/2-Methyl-1-butanol "2-Methyl-1-butanol")
- [Ethanol](/wiki/Ethanol "Ethanol")
- [Isoamyl alcohol](/wiki/Isoamyl_alcohol "Isoamyl alcohol")
- [Isobutanol](/wiki/Isobutanol "Isobutanol")
- [Phenethyl alcohol](/wiki/Phenethyl_alcohol "Phenethyl alcohol")
- [_tert_-Amyl alcohol](/wiki/Tert-Amyl_alcohol "Tert-Amyl alcohol")
- [_tert_-Butyl alcohol](/wiki/Tert-Butyl_alcohol "Tert-Butyl alcohol")
- [Tryptophol](/wiki/Tryptophol "Tryptophol")

[Medical alcohol](/wiki/Alcohols_(medicine) "Alcohols (medicine)")

- [Ethchlorvynol](/wiki/Ethchlorvynol "Ethchlorvynol")
- [Methylpentynol](/wiki/Methylpentynol "Methylpentynol")
- Methanol poisoning
  - [Ethanol](/wiki/Ethanol "Ethanol")

[Toxic alcohols](/wiki/Toxic_alcohol "Toxic alcohol")

- [Isopropyl alcohol](/wiki/Isopropyl_alcohol "Isopropyl alcohol")
- [Methanol](/wiki/Methanol "Methanol")

[Primary\
\
alcohols](/wiki/Primary_alcohol "Primary alcohol") (1°)

[Methanol](/wiki/Methanol "Methanol")

- [4-Methylcyclohexanemethanol](/wiki/4-Methylcyclohexanemethanol "4-Methylcyclohexanemethanol")
- [Aminomethanol](/wiki/Aminomethanol "Aminomethanol")
- [Cyclohexylmethanol](/wiki/Cyclohexylmethanol "Cyclohexylmethanol")
- [Methoxymethanol](/wiki/Methoxymethanol "Methoxymethanol")
- [Methylazoxymethanol](/wiki/Methylazoxymethanol "Methylazoxymethanol")
- [Trifluoromethanol](/wiki/Trifluoromethanol "Trifluoromethanol")

[Ethanol](/wiki/Ethanol "Ethanol")

- [1-Aminoethanol](/wiki/1-Aminoethanol "1-Aminoethanol")
- [2,2,2-Trichloroethanol](/wiki/2,2,2-Trichloroethanol "2,2,2-Trichloroethanol")
- [2,2,2-Trifluoroethanol](/wiki/2,2,2-Trifluoroethanol "2,2,2-Trifluoroethanol")
- [2-(2-Ethoxyethoxy)ethanol](/wiki/2-(2-Ethoxyethoxy)ethanol "2-(2-Ethoxyethoxy)ethanol")
- [2-(2-Methoxyethoxy)ethanol](/wiki/2-(2-Methoxyethoxy)ethanol "2-(2-Methoxyethoxy)ethanol")
- [2-(2-Methoxyethoxy)ethanol](/wiki/2-(2-Methoxyethoxy)ethanol "2-(2-Methoxyethoxy)ethanol")
- [2-Butoxyethanol](/wiki/2-Butoxyethanol "2-Butoxyethanol")
- [2-Chloroethanol](/wiki/2-Chloroethanol "2-Chloroethanol")
- [2-Ethoxyethanol](/wiki/2-Ethoxyethanol "2-Ethoxyethanol")
- [2-Fluoroethanol](/wiki/2-Fluoroethanol "2-Fluoroethanol")
- [2-Mercaptoethanol](/wiki/2-Mercaptoethanol "2-Mercaptoethanol")
- [2-Methoxyethanol](/wiki/2-Methoxyethanol "2-Methoxyethanol")
- [Aminoethylethanolamine](/wiki/Aminoethylethanolamine "Aminoethylethanolamine")
- [Diethylethanolamine](/wiki/Diethylethanolamine "Diethylethanolamine")
- [Dimethylethanolamine](/wiki/Dimethylethanolamine "Dimethylethanolamine")
- [Ethanol](/wiki/Ethanol "Ethanol")
- [Ethanolamine](/wiki/Ethanolamine "Ethanolamine")
- [_N_, _N_-Diisopropylaminoethanol](/wiki/N,N-Diisopropylaminoethanol "N,N-Diisopropylaminoethanol")
- [_N_-Methylethanolamine](/wiki/N-Methylethanolamine "N-Methylethanolamine")
- [Phenoxyethanol](/wiki/Phenoxyethanol "Phenoxyethanol")
- [Tribromoethanol](/wiki/Tribromoethanol "Tribromoethanol")

[Butanol](/wiki/Butanol "Butanol")

- [2-Methyl-1-butanol](/wiki/2-Methyl-1-butanol "2-Methyl-1-butanol")
- [Isobutanol](/wiki/Isobutanol "Isobutanol")
- [_n_-Butanol](/wiki/N-Butanol "N-Butanol")

Straight-chain

saturated

C1 — C9

- [Methanol](/wiki/Methanol "Methanol")
- [Ethanol](/wiki/Ethanol "Ethanol")
- [1-Propanol](/wiki/1-Propanol "1-Propanol")
- [1-Butanol](/wiki/1-Butanol "1-Butanol")
- [1-Pentanol](/wiki/1-Pentanol "1-Pentanol")
- [1-Hexanol](/wiki/1-Hexanol "1-Hexanol")
- [1-Heptanol](/wiki/1-Heptanol "1-Heptanol")
- [1-Octanol](/wiki/1-Octanol "1-Octanol") (capryl)
- [1-Nonanol](/wiki/1-Nonanol "1-Nonanol") (pelargonic)

Straight-chain

saturated

C10 — C19

- [1-Decanol](/wiki/1-Decanol "1-Decanol") (capric)
- [1-Undecanol](/wiki/1-Undecanol "1-Undecanol") (hendecyl)
- [1-Dodecanol](/wiki/1-Dodecanol "1-Dodecanol") (lauryl)
- [1-Tridecanol](/wiki/1-Tridecanol "1-Tridecanol")
- [1-Tetradecanol](/wiki/1-Tetradecanol "1-Tetradecanol") (myristyl)
- [1-Pentadecanol](/wiki/1-Pentadecanol "1-Pentadecanol")
- [1-Hexadecanol](/wiki/1-Hexadecanol "1-Hexadecanol") (cetyl / palmityl)
- [1-Heptadecanol](/wiki/1-Heptadecanol "1-Heptadecanol")
- [1-Octadecanol](/wiki/1-Octadecanol "1-Octadecanol") (stearyl)
- [1-Nonadecanol](/wiki/1-Nonadecanol "1-Nonadecanol")

Straight-chain

saturated

C20 — C29

- [1-Icosanol](/wiki/1-Icosanol "1-Icosanol") (arachidyl)
- [1-Heneicosanol](/wiki/1-Heneicosanol "1-Heneicosanol")
- [1-Docosanol](/wiki/1-Docosanol "1-Docosanol") (behenyl)
- [1-Tricosanol](/w/index.php?title=1-Tricosanol&action=edit&redlink=1 "1-Tricosanol (page does not exist)")
- [1-Tetracosanol](/wiki/1-Tetracosanol "1-Tetracosanol") (lignoceryl)
- [1-Pentacosanol](/w/index.php?title=1-Pentacosanol&action=edit&redlink=1 "1-Pentacosanol (page does not exist)")
- [1-Hexacosanol](/wiki/1-Hexacosanol "1-Hexacosanol") (ceryl)
- [1-Heptacosanol](/wiki/1-Heptacosanol "1-Heptacosanol")
- [1-Octacosanol](/wiki/1-Octacosanol "1-Octacosanol") (cluytyl / montanyl)
- [1-Nonacosanol](/wiki/1-Nonacosanol "1-Nonacosanol")

Straight-chain

saturated

C30 — C39

- [1-Triacontanol](/wiki/1-Triacontanol "1-Triacontanol") (melissyl / myricyl)
- [1-Hentriacontanol](/w/index.php?title=1-Hentriacontanol&action=edit&redlink=1 "1-Hentriacontanol (page does not exist)")
- [1-Dotriacontanol](/wiki/1-Dotriacontanol "1-Dotriacontanol") (lacceryl)
- [1-Tritriacontanol](/w/index.php?title=1-Tritriacontanol&action=edit&redlink=1 "1-Tritriacontanol (page does not exist)")
- [1-Tetratriacontanol](/w/index.php?title=1-Tetratriacontanol&action=edit&redlink=1 "1-Tetratriacontanol (page does not exist)") (geddyl)
- [1-Pentatriacontanol](/w/index.php?title=1-Pentatriacontanol&action=edit&redlink=1 "1-Pentatriacontanol (page does not exist)")
- [1-Hexatriacontanol](/w/index.php?title=1-Hexatriacontanol&action=edit&redlink=1 "1-Hexatriacontanol (page does not exist)")
- [1-Heptatriacontanol](/w/index.php?title=1-Heptatriacontanol&action=edit&redlink=1 "1-Heptatriacontanol (page does not exist)")
- [1-Octatriacontanol](/w/index.php?title=1-Octatriacontanol&action=edit&redlink=1 "1-Octatriacontanol (page does not exist)")
- [1-Nonatriacontanol](/w/index.php?title=1-Nonatriacontanol&action=edit&redlink=1 "1-Nonatriacontanol (page does not exist)")

Straight-chain

saturated

C40 — C49

- [1-Tetracontanol](/w/index.php?title=1-Tetracontanol&action=edit&redlink=1 "1-Tetracontanol (page does not exist)")
- [1-Hentetracontanol](/w/index.php?title=1-Hentetracontanol&action=edit&redlink=1 "1-Hentetracontanol (page does not exist)")
- [1-Dotetracontanol](/w/index.php?title=1-Dotetracontanol&action=edit&redlink=1 "1-Dotetracontanol (page does not exist)")
- [1-Tritetracontanol](/w/index.php?title=1-Tritetracontanol&action=edit&redlink=1 "1-Tritetracontanol (page does not exist)")
- [1-Tetratetracontanol](/w/index.php?title=1-Tetratetracontanol&action=edit&redlink=1 "1-Tetratetracontanol (page does not exist)")
- [1-Pentatetracontanol](/w/index.php?title=1-Pentatetracontanol&action=edit&redlink=1 "1-Pentatetracontanol (page does not exist)")
- [1-Hexatetracontanol](/w/index.php?title=1-Hexatetracontanol&action=edit&redlink=1 "1-Hexatetracontanol (page does not exist)")
- [1-Heptatetracontanol](/w/index.php?title=1-Heptatetracontanol&action=edit&redlink=1 "1-Heptatetracontanol (page does not exist)")
- [1-Octatetracontanol](/w/index.php?title=1-Octatetracontanol&action=edit&redlink=1 "1-Octatetracontanol (page does not exist)")
- [1-Nonatetracontanol](/w/index.php?title=1-Nonatetracontanol&action=edit&redlink=1 "1-Nonatetracontanol (page does not exist)")

- [2-Ethylhexanol](/wiki/2-Ethylhexanol "2-Ethylhexanol")
- [Allyl alcohol](/wiki/Allyl_alcohol "Allyl alcohol")
- [Anisyl alcohol](/wiki/Anisyl_alcohol "Anisyl alcohol")
- Benzyl alcohol
- [Cinnamyl alcohol](/wiki/Cinnamyl_alcohol "Cinnamyl alcohol")
- [Crotyl alcohol](/wiki/Crotyl_alcohol "Crotyl alcohol")
- [Furfuryl alcohol](/wiki/Furfuryl_alcohol "Furfuryl alcohol")
- [Isoamyl alcohol](/wiki/Isoamyl_alcohol "Isoamyl alcohol")
- [Neopentyl alcohol](/wiki/Neopentyl_alcohol "Neopentyl alcohol")
- [Nicotinyl alcohol](/wiki/Nicotinyl_alcohol "Nicotinyl alcohol")
- [Perillyl alcohol](/wiki/Perillyl_alcohol "Perillyl alcohol")
- [Phenethyl alcohol](/wiki/Phenethyl_alcohol "Phenethyl alcohol")
- [Prenol](/wiki/Prenol "Prenol")
- [Propargyl alcohol](/wiki/Propargyl_alcohol "Propargyl alcohol")
- [Salicyl alcohol](/wiki/Salicyl_alcohol "Salicyl alcohol")
- [Tryptophol](/wiki/Tryptophol "Tryptophol")
- [Vanillyl alcohol](/wiki/Vanillyl_alcohol "Vanillyl alcohol")
- [Veratrole alcohol](/wiki/Veratrole_alcohol "Veratrole alcohol")

Secondary

alcohols (2°)

[1-Phenylethanol](/wiki/1-Phenylethanol "1-Phenylethanol")
[2-Butanol](/wiki/2-Butanol "2-Butanol")
[2-Deoxyerythritol](/w/index.php?title=2-Deoxyerythritol&action=edit&redlink=1 "2-Deoxyerythritol (page does not exist)")
[2-Heptanol](/wiki/2-Heptanol "2-Heptanol")
[3-Heptanol](/wiki/3-Heptanol "3-Heptanol")
[2-Hexanol](/wiki/2-Hexanol "2-Hexanol")
[3-Hexanol](/wiki/3-Hexanol "3-Hexanol")
[3-Methyl-2-butanol](/wiki/3-Methyl-2-butanol "3-Methyl-2-butanol")
[2-Nonanol](/wiki/2-Nonanol "2-Nonanol")
[2-Octanol](/wiki/2-Octanol "2-Octanol")
[2-Pentanol](/wiki/2-Pentanol "2-Pentanol")
[3-Pentanol](/wiki/3-Pentanol "3-Pentanol")
[Cyclohexanol](/wiki/Cyclohexanol "Cyclohexanol")
[Cyclopentanol](/wiki/Cyclopentanol "Cyclopentanol")
[Cyclopropanol](/wiki/Cyclopropanol "Cyclopropanol")
[Diphenylmethanol](/wiki/Diphenylmethanol "Diphenylmethanol")
[Isopropanol](/wiki/Isopropyl_alcohol "Isopropyl alcohol")
[Pinacolyl alcohol](/wiki/Pinacolyl_alcohol "Pinacolyl alcohol")
[Pirkle's alcohol](/wiki/Pirkle%27s_alcohol "Pirkle's alcohol")
[Propylene glycol methyl ether](/wiki/Propylene_glycol_methyl_ether "Propylene glycol methyl ether")

Tertiary

alcohols (3°)

- [2-Methyl-2-pentanol](/wiki/2-Methyl-2-pentanol "2-Methyl-2-pentanol")
- [2-Methylheptan-2-ol](/w/index.php?title=2-Methylheptan-2-ol&action=edit&redlink=1 "2-Methylheptan-2-ol (page does not exist)")
- [2-Methylhexan-2-ol](/w/index.php?title=2-Methylhexan-2-ol&action=edit&redlink=1 "2-Methylhexan-2-ol (page does not exist)")
- [3-Methyl-3-pentanol](/wiki/3-Methyl-3-pentanol "3-Methyl-3-pentanol")
- [3-Methyloctan-3-ol](/w/index.php?title=3-Methyloctan-3-ol&action=edit&redlink=1 "3-Methyloctan-3-ol (page does not exist)")
- [Diacetone alcohol](/wiki/Diacetone_alcohol "Diacetone alcohol")
- [Ethchlorvynol](/wiki/Ethchlorvynol "Ethchlorvynol")
- [Methylpentynol](/wiki/Methylpentynol "Methylpentynol")
- [Nonafluoro- _tert_-butyl alcohol](/wiki/Nonafluoro-tert-butyl_alcohol "Nonafluoro-tert-butyl alcohol")
- [_tert_-Amyl alcohol](/wiki/Tert-Amyl_alcohol "Tert-Amyl alcohol")
- [_tert_-Butyl alcohol](/wiki/Tert-Butyl_alcohol "Tert-Butyl alcohol")
- [Triphenylethanol](/wiki/Triphenylethanol "Triphenylethanol")
- [Triphenylmethanol](/wiki/Triphenylmethanol "Triphenylmethanol")

Hydric alcohols

Monohydric alcohols

- [Methanol](/wiki/Methanol "Methanol") (C1)
- [Ethanol](/wiki/Ethanol "Ethanol") (C2)
- [Isopropanol](/wiki/Isopropanol "Isopropanol") (C3)
- [1-Butanol](/wiki/1-Butanol "1-Butanol") (C4)
- [1-Pentanol](/wiki/1-Pentanol "1-Pentanol") (C5)
- [Cetyl alcohol](/wiki/Cetyl_alcohol "Cetyl alcohol") (C16)

Dihydric alcohols

- [Ethylene glycol](/wiki/Ethylene_glycol "Ethylene glycol")
- [Propylene glycol](/wiki/Propylene_glycol "Propylene glycol")

Trihydric alcohols

- [Glycerol](/wiki/Glycerol "Glycerol")

[Polyhydric alcohols (sugar alcohols)](/wiki/Sugar_alcohol "Sugar alcohol")

- [Pentaerythritol](/wiki/Pentaerythritol "Pentaerythritol")
- [Ethylene glycol](/wiki/Ethylene_glycol "Ethylene glycol") (C2)
- [Glycerol](/wiki/Glycerol "Glycerol"), [Propylene glycol](/wiki/Propylene_glycol "Propylene glycol") (C3)
- [Erythritol](/wiki/Erythritol "Erythritol"), [Threitol](/wiki/Threitol "Threitol") (C4)
- [Xylitol](/wiki/Xylitol "Xylitol") (C5)
- [Mannitol](/wiki/Mannitol "Mannitol"), [Sorbitol](/wiki/Sorbitol "Sorbitol") (C6)
- [Volemitol](/wiki/Volemitol "Volemitol") (C7)

[Amyl alcohols](/wiki/Amyl_alcohol "Amyl alcohol")

- [2,2-Dimethylpropan-1-ol](/wiki/2,2-Dimethylpropan-1-ol "2,2-Dimethylpropan-1-ol")
- [2-Methylbutan-1-ol](/wiki/2-Methylbutan-1-ol "2-Methylbutan-1-ol")
- [2-Methylbutan-2-ol](/wiki/2-Methylbutan-2-ol "2-Methylbutan-2-ol")
- [3-Methylbutan-1-ol](/wiki/3-Methylbutan-1-ol "3-Methylbutan-1-ol")
- [3-Methylbutan-2-ol](/wiki/3-Methylbutan-2-ol "3-Methylbutan-2-ol")
- [Pentan-1-ol](/wiki/Pentan-1-ol "Pentan-1-ol")
- [Pentan-2-ol](/wiki/Pentan-2-ol "Pentan-2-ol")
- [Pentan-3-ol](/wiki/Pentan-3-ol "Pentan-3-ol")

[Aromatic alcohols](/wiki/Alcohol_(chemistry) "Alcohol (chemistry)")

- Benzyl alcohol
- [2,4-Dichlorobenzyl alcohol](/wiki/2,4-Dichlorobenzyl_alcohol "2,4-Dichlorobenzyl alcohol")
- [3-Nitrobenzyl alcohol](/wiki/3-Nitrobenzyl_alcohol "3-Nitrobenzyl alcohol")

Saturated

[fatty alcohols](/wiki/Fatty_alcohol "Fatty alcohol")

- [Cetostearyl alcohol](/wiki/Cetostearyl_alcohol "Cetostearyl alcohol")
- [Decanol](/wiki/Decanol "Decanol")
- [Lauryl alcohol](/wiki/Lauryl_alcohol "Lauryl alcohol")
- [Myristyl alcohol](/wiki/Myristyl_alcohol "Myristyl alcohol")
- [Nonanol](/wiki/Nonanol_(disambiguation) "Nonanol (disambiguation)")
- [Octanol](/wiki/Octanol "Octanol")
- [Tridecanol](/wiki/Tridecanol "Tridecanol")
- [Undecanol](/wiki/Undecanol "Undecanol")

Branched and

unsaturated

[fatty alcohols](/wiki/Fatty_alcohol "Fatty alcohol")

- [3-Methyl-3-pentanol](/wiki/3-Methyl-3-pentanol "3-Methyl-3-pentanol")
- [Erucyl alcohol](/w/index.php?title=Erucyl_alcohol&action=edit&redlink=1 "Erucyl alcohol (page does not exist)")
- [Linolenyl alcohol](/w/index.php?title=Linolenyl_alcohol&action=edit&redlink=1 "Linolenyl alcohol (page does not exist)")
- [Linoleyl alcohol](/wiki/Linoleyl_alcohol "Linoleyl alcohol")
- [Oleyl alcohol](/wiki/Oleyl_alcohol "Oleyl alcohol")
- [Palmitoleyl alcohol](/w/index.php?title=Palmitoleyl_alcohol&action=edit&redlink=1 "Palmitoleyl alcohol (page does not exist)")
- [tert-Amyl alcohol](/wiki/Tert-Amyl_alcohol "Tert-Amyl alcohol")
- [tert-Butyl alcohol](/wiki/Tert-Butyl_alcohol "Tert-Butyl alcohol")

[Sugar alcohols](/wiki/Sugar_alcohol "Sugar alcohol")

C1 — C7

- [Methylene glycol](/wiki/Methylene_glycol "Methylene glycol") (C1)
- [Ethylene glycol](/wiki/Ethylene_glycol "Ethylene glycol") (C2)
- [Glycerol](/wiki/Glycerol "Glycerol") (C3)
- [Erythritol](/wiki/Erythritol "Erythritol") (C4)
- [Threitol](/wiki/Threitol "Threitol") (C4)
- [Arabitol](/wiki/Arabitol "Arabitol") (C5)
- [Ribitol](/wiki/Ribitol "Ribitol") (C5)
- [Xylitol](/wiki/Xylitol "Xylitol") (C5)
- [Mannitol](/wiki/Mannitol "Mannitol") (C6)
- [Sorbitol](/wiki/Sorbitol "Sorbitol") (C6)
- [Galactitol](/wiki/Galactitol "Galactitol") (C6)
- [Iditol](/wiki/Iditol "Iditol") (C6)
- [Volemitol](/wiki/Volemitol "Volemitol") (C7)

Deoxy sugar

alcohols

- [Fucitol](/wiki/Fucitol "Fucitol")

Cyclic sugar

alcohols

- [Inositol](/wiki/Inositol "Inositol")

Glycylglycitols

- [Maltitol](/wiki/Maltitol "Maltitol")
- [Lactitol](/wiki/Lactitol "Lactitol")
- [Isomalt](/wiki/Isomalt "Isomalt")
- [Maltotriitol](/w/index.php?title=Maltotriitol&action=edit&redlink=1 "Maltotriitol (page does not exist)")
- [Maltotetraitol](/w/index.php?title=Maltotetraitol&action=edit&redlink=1 "Maltotetraitol (page does not exist)")
- [Polyglycitol](/w/index.php?title=Polyglycitol&action=edit&redlink=1 "Polyglycitol (page does not exist)")

Terpene alcohols

Monoterpene

alcohols

- [Borneol](/wiki/Borneol "Borneol")
- [Citronellol](/wiki/Citronellol "Citronellol")
- [Geraniol](/wiki/Geraniol "Geraniol")
- [Linalool](/wiki/Linalool "Linalool")
- [Menthol](/wiki/Menthol "Menthol")
- [Nerol](/wiki/Nerol "Nerol")
- [Rhodinol](/wiki/Rhodinol "Rhodinol")
- [Terpineol](/wiki/Terpineol "Terpineol")

Sesquiterpene

alcohols

- [Bisabolol](/wiki/Bisabolol "Bisabolol")
- [Farnesol](/wiki/Farnesol "Farnesol")
- [Nerolidol](/wiki/Nerolidol "Nerolidol")
- [Patchoulol](/wiki/Patchoulol "Patchoulol")

Diterpene

alcohols

- [Phytol](/wiki/Phytol "Phytol")

Dialcohols

- [1,4-Butanediol](/wiki/1,4-Butanediol "1,4-Butanediol")
- [1,5-Pentanediol](/wiki/1,5-Pentanediol "1,5-Pentanediol")
- [2-Methyl-2-propyl-1,3-propanediol](/wiki/2-Methyl-2-propyl-1,3-propanediol "2-Methyl-2-propyl-1,3-propanediol")
- [Diethylpropanediol](/wiki/Diethylpropanediol "Diethylpropanediol")
- [Ethylene glycol](/wiki/Ethylene_glycol "Ethylene glycol")

Trialcohols

- [Glycerol](/wiki/Glycerol "Glycerol")

Sterols

- [Cholesterol](/wiki/Cholesterol "Cholesterol")
- [Ergosterol](/wiki/Ergosterol "Ergosterol")
- [Lanosterol](/wiki/Lanosterol "Lanosterol")
- [β-Sitosterol](/wiki/Beta-Sitosterol "Beta-Sitosterol")
- [Stigmasterol](/wiki/Stigmasterol "Stigmasterol")

[Fluoroalcohols](/wiki/Fluoroalcohol "Fluoroalcohol")

- [1,3-Difluoro-2-propanol](/wiki/1,3-Difluoro-2-propanol "1,3-Difluoro-2-propanol")
- [2,2,2-Trifluoroethanol](/wiki/2,2,2-Trifluoroethanol "2,2,2-Trifluoroethanol")
- [2-Fluoroethanol](/wiki/2-Fluoroethanol "2-Fluoroethanol")
- [Nonafluoro- _tert_-butyl alcohol](/wiki/Nonafluoro-tert-butyl_alcohol "Nonafluoro-tert-butyl alcohol")
- [Trifluoromethanol](/wiki/Trifluoromethanol "Trifluoromethanol")

Preparations

- [Substitution](/wiki/Substitution_reaction "Substitution reaction") of [haloalkane](/wiki/Haloalkane#Substitution "Haloalkane")
- [Carbonyl reduction](/wiki/Carbonyl_reduction "Carbonyl reduction")
- [Ether cleavage](/wiki/Ether_cleavage "Ether cleavage")
- [Hydrolysis](/wiki/Hydrolysis "Hydrolysis") of [epoxide](/wiki/Epoxide#Hydrolysis_and_addition_of_nucleophiles "Epoxide")
- [Hydration](/wiki/Hydration_reaction "Hydration reaction") of [alkene](/wiki/Alkene#Hydration "Alkene")
- [Ziegler process](/wiki/Ziegler_process "Ziegler process")

Reactions

- [Deprotonation](/wiki/Deprotonation "Deprotonation")
- [Protonation](/wiki/Protonation "Protonation")
- [Alcohol oxidation](/wiki/Alcohol_oxidation "Alcohol oxidation")
  - [Glycol cleavage](/wiki/Glycol_cleavage "Glycol cleavage")
- [Nucleophilic substitution](/wiki/Nucleophilic_substitution "Nucleophilic substitution")
- [Fischer–Speier esterification](/wiki/Fischer%E2%80%93Speier_esterification "Fischer–Speier esterification")
- [Williamson ether synthesis](/wiki/Williamson_ether_synthesis "Williamson ether synthesis")
- [Elimination reaction](/wiki/Elimination_reaction "Elimination reaction")
- [Nucleophilic substitution](/wiki/Nucleophilic_substitution "Nucleophilic substitution") of [carbonyl group](/wiki/Carbonyl_group "Carbonyl group")
- [Friedel-Crafts alkylation](/wiki/Friedel-Crafts_alkylation "Friedel-Crafts alkylation")
- [Nucleophilic conjugate addition](/wiki/Nucleophilic_conjugate_addition "Nucleophilic conjugate addition")
- [Transesterification](/wiki/Transesterification "Transesterification")

- ![](//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png)[Category](/wiki/Category:Alcohols "Category:Alcohols")

[Portal](/wiki/Wikipedia:Contents/Portals "Wikipedia:Contents/Portals"):

- ![icon](//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/WHO_Rod.svg/8px-WHO_Rod.svg.png)[Medicine](/wiki/Portal:Medicine "Portal:Medicine")

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- [Germany](https://d-nb.info/gnd/4336686-7)
- [France](https://catalogue.bnf.fr/ark:/12148/cb155215133)
- [BnF data](https://data.bnf.fr/ark:/12148/cb155215133)

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[Categories](/wiki/Help:Category "Help:Category"):

- [Flavors](/wiki/Category:Flavors "Category:Flavors")
- [Primary alcohols](/wiki/Category:Primary_alcohols "Category:Primary alcohols")
- [Alcohol solvents](/wiki/Category:Alcohol_solvents "Category:Alcohol solvents")
- [Perfume ingredients](/wiki/Category:Perfume_ingredients "Category:Perfume ingredients")
- [Aromatic solvents](/wiki/Category:Aromatic_solvents "Category:Aromatic solvents")
- [Benzyl compounds](/wiki/Category:Benzyl_compounds "Category:Benzyl compounds")
- [E-number additives](/wiki/Category:E-number_additives "Category:E-number additives")
- [Antimicrobials](/wiki/Category:Antimicrobials "Category:Antimicrobials")

Hidden categories:

- [Articles with short description](/wiki/Category:Articles_with_short_description "Category:Articles with short description")
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- [Use dmy dates from April 2020](/wiki/Category:Use_dmy_dates_from_April_2020 "Category:Use dmy dates from April 2020")
- [Chemical articles with multiple compound IDs](/wiki/Category:Chemical_articles_with_multiple_compound_IDs "Category:Chemical articles with multiple compound IDs")
- [Multiple chemicals in an infobox that need indexing](/wiki/Category:Multiple_chemicals_in_an_infobox_that_need_indexing "Category:Multiple chemicals in an infobox that need indexing")
- [ECHA InfoCard ID from Wikidata](/wiki/Category:ECHA_InfoCard_ID_from_Wikidata "Category:ECHA InfoCard ID from Wikidata")
- [E number from Wikidata](/wiki/Category:E_number_from_Wikidata "Category:E number from Wikidata")
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- [Short description matches Wikidata](/wiki/Category:Short_description_matches_Wikidata "Category:Short description matches Wikidata")

- This page was last edited on 11 September 2024, at 14:26 (UTC).
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