2-hexanol

General Material Information

Preferred name	2-hexanol
Trivial Name	(±)-2-Hexanol
Short Description	(±)-2-hexanol
Formula	C6 H14 O
CAS Number	626-93-7
Deleted CAS Number	20281-86-1
ECHA Number	210-971-4
FDA UNII	9CDT0V6T4P
Nikkaji Number	J1.693D
Beilstein Number	1718996
MDL	MFCD00004585
COE Number	11774
NMR Predictor	External link
Synonyms	butyl methyl carbinol hexan-2-ol N- hexan-2-ol (±)-2-hexanol 2-hexanol, (±)- 2-hydroxyhexane methylamyl alcohol methylpentanol pentanol, methyl- 2-Hydroxyhexane (±)-2-Hexanol DL-Hexan-2-ol (±)-1-Methyl-1-pentanol NSC 3706 1-Methyl-1-pentanol

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Literature & References

Leffingwell:	Chirality or Article
	hexan-2-ol
NIST Chemistry WebBook:	Search Inchi
Canada Domestic Sub. List:	626-93-7
Pubchem (cid):	12297
Pubchem (sid):	134978502
Pherobase:	View

Publications by PubMed
Differential involvement of glutamate-gated chloride channel splice variants in the olfactory memory processes of the honeybee Apis mellifera.
Redox self-sufficient whole cell biotransformation for amination of alcohols.
Copper-organic frameworks assembled from in situ generated 5-(4-pyridyl)tetrazole building blocks: synthesis, structural features, topological analysis and catalytic oxidation of alcohols.
Effect of compression on the relationship between viscosity and dielectric relaxation time in hydrogen-bonded primary alcohols.
Antimicrobial Potential and Chemical Characterization of Serbian Liverwort (Porella arboris-vitae): SEM and TEM Observations.
Volatile compounds emitted by Triatoma dimidiata, a vector of Chagas disease: chemical analysis and behavioural evaluation.
Influence of cultivation parameters on the composition of volatile compounds and physico-chemical characteristics of kiwi fruit.
Borenium ion catalyzed hydroboration of alkenes with N-heterocyclic carbene-boranes.
Synergism between microwave irradiation and enzyme catalysis in transesterification of ethyl-3-phenylpropanoate with n-butanol.
Enantioselective degradation of hexaconazole in rat hepatic microsomes in vitro.
Effect of high hydrostatic pressure on the dielectric relaxation in a non-crystallizable monohydroxy alcohol in its supercooled liquid and glassy states.
Selective hydroxylation of alkanes by an extracellular fungal peroxygenase.
Exploring natural products for new taste sensations.
Debye process and dielectric state of an alcohol in a nonpolar solvent.
Synthesis of conformationally locked L-deoxythreosyl phosphonate nucleosides built on a bicyclo[3.1.0]hexane template.
A greener enantioselective synthesis of the antiviral agent North-methanocarbathymidine (N-MCT) from 2-deoxy-d-ribose.
Degradation of hexane and other recalcitrant hydrocarbons by a novel isolate, Rhodococcus sp. EH831.
The effect of co-surfactant-modified micelles on chiral separations in EKC.
Specific heat relaxation of an alcohol and implications for dielectric comparison.
Volatile compounds in dry-cured Serrano ham subjected to high pressure processing. Effect of the packaging material.
Effect of microemulsion component purity on the chromatographic figures of merit in chiral microemulsion electrokinetic chromatography.
Synthesis, crystallization mechanism, and catalytic properties of titanium-rich TS-1 free of extraframework titanium species.
Structure-dependent dc conductivity and relaxation time in the Debye-Stokes-Einstein equation.
Influence of microemulsion chirality on chromatographic figures of merit in EKC: results with novel three-chiral-component microemulsions and comparison with one- and two-chiral-component microemulsions.
Two-chiral component microemulsion EKC - chiral surfactant and chiral oil. Part 2: diethyl tartrate.
Two-chiral-component microemulsion electrokinetic chromatography-chiral surfactant and chiral oil: part 1. dibutyl tartrate.
Intramolecular cyclopropanation of unsaturated terminal epoxides and chlorohydrins.
Purification and characterization of alcohol dehydrogenase reducing N-benzyl-3-pyrrolidinone from Geotrichum capitatum.
Degradation of alkyl methyl ketones by Pseudomonas veronii MEK700.
Relaxations and nano-phase-separation in ultraviscous heptanol-alkyl halide mixture.
Chiral microemulsion electrokinetic chromatography: Effect of cosurfactant identity on enantioselectivity, methylene selectivity, resolution, and other chromatographic figures of merit.
Uptake of organic gas phase species by 1-methylnaphthalene.
Chirality in anesthesia II: stereoselective modulation of ion channel function by secondary alcohol enantiomers.
Chirality in anesthesia I: minimum alveolar concentration of secondary alcohol enantiomers.
Chiral microemulsion electrokinetic chromatography with two chiral components: Improved separations via synergies between a chiral surfactant and a chiral cosurfactant.
Speed of sound measurements conducted at high pressures on aqueous alcohol and aqueous diol systems at T = 298.15 K.
Stereoselective kinetic study of hexaconazole enantiomers in the rabbit.
Dynamics of glass-forming liquids. VIII. Dielectric signature of probe rotation and bulk dynamics in branched alkanes.
Separation of enantiomers in microemulsion electrokinetic chromatography using chiral alcohols as cosurfactants.
Epoxide hydrolase: a mRNA induced by the fungal pathogen Alternaria alternata on rough lemon (Citrus jambhiri Lush).
Direct observation of odd-even effect for chiral alkyl alcohols in solution using vibrational circular dichroism spectroscopy.
Microemulsion electrokinetic chromatography for the analysis of green tea catechins: effect of the cosurfactant on the separation selectivity.
On the mechanism of the unexpected facile formation of meso-diacetate products in enzymatic acetylation of alkanediols.
Olfactory discrimination of structurally similar alcohols by cockroaches.
Sorption behavior of triazole fungicides in Indian soils and its correlation with soil properties.
Aroma active components in aqueous kiwi fruit essence and kiwi fruit puree by GC-MS and multidimensional GC/GC-O.
Enantioselective synthesis of bicyclo[3.1.0]hexane carbocyclic nucleosides via a lipase-catalyzed asymmetric acetylation. Characterization of an unusual acetal byproduct.
Synthesis and Characterization of Basic Catalysts Based on Sodium-Magnesium Mixed Phosphates and Their Use in the Conversion of 2-Hexanol.
Fragrance volatiles of developing and senescing carnation flowers.
Headspace analysis of engine oil by gas chromatography/mass spectrometry.
Persistence of hexaconazole, a triazole fungicide in soils.
NAD(+)-dependent (S)-specific secondary alcohol dehydrogenase involved in stereoinversion of 3-pentyn-2-ol catalyzed by Nocardia fusca AKU 2123.
Synthesis, Characterization, and Catalytic Uses of Mg(3)(PO(4))(2)/MgO Systems.
Determination of free and glucuronated hexane metabolites without prior hydrolysis by liquid- and gas-chromatography coupled with mass spectrometry.
Synthesis and Characterization of Magnesium Phosphates and Their Catalytic Properties in the Conversion of 2-Hexanol.
Determination of n-hexane metabolites by liquid chromatography/mass spectrometry. 2. Glucuronide-conjugated metabolites in untreated urine samples by electrospray ionization.
Odour coding is bilaterally symmetrical in the antennal lobes of honeybees (Apis mellifera).
Metabolic interaction of n-hexane and methyl ethyl ketone in vitro in a head space rat liver S9 vial equilibration system.
Comparison and in vivo relevance of two different in vitro head space metabolic systems: liver S9 and liver slices.
Subcellular Localization of Secondary Lipid Metabolites Including Fragrance Volatiles in Carnation Petals.
An investigation into the role of rat skeletal muscle as a site for xenobiotic metabolism using microsomes and isolated cells.
Metabolism of n-hexane by rat liver and extrahepatic tissues and the effect of cytochrome P-450 inducers.
Effects of n-hexane and its metabolites on cloned voltage-operated neuronal potassium channels.
Method for the simultaneous quantification of n-hexane metabolites: application to n-hexane metabolism determination.
Toxic effects of hexane derivatives on cultured rat Schwann cells.
In vitro quantitative structure-activity relationship assessment of pyrrole adducts production by gamma-diketone-forming neurotoxic solvents.
Tissue concentrations of methyl isobutyl ketone, methyl n-butyl ketone and their metabolites after oral or inhalation exposure.
Pharmacodynamic and metabolic interactions between ethanol and two industrial solvents (methyl n-butyl ketone and methyl isobutyl ketone) and their principal metabolites in mice.
Metabolic fate of methyl n-butyl ketone, methyl isobutyl ketone and their metabolites in mice.
Isolation of acylcarnitines from urine: a comparison of methods and application to long-chain acyl-CoA dehydrogenase deficiency.
Effect of tuamine, heptaminol and two analogues on uptake and release of catecholamines in cultured chromaffin cells.
Changes in urinary n-hexane metabolites by co-exposure to various concentrations of methyl ethyl ketone and fixed n-hexane levels.
The in vitro effects of alkanes, alcohols, and ketones on rat lung cytochrome P450-dependent alkoxyphenoxazone dealkylase activities.
The relevance of 4,5-dihydroxy-2-hexanone in the excretion kinetics of n-hexane metabolites in rat and man.
Resolution of enantiomeric amides on a cellulose tribenzoate chiral stationary phase. Mobile phase modifier effects on retention and stereo-selectivity.
Anesthetic potencies of secondary alcohol enantiomers.
Urinary excretion of 2,5-hexanedione and peripheral polyneuropathies workers exposed to hexane.
Rat lung and liver microsomal cytochrome P-450 isozymes involved in the hydroxylation of n-hexane.
Phthalate esters: effects of orally administered dibutylphthalate on cytochrome P-450 mediated metabolism in rat liver and lung.
Metabolites and ketone body production following methyl n-butyl ketone exposure as possible indices of MnBK potentiation of carbon tetrachloride hepatotoxicity.
Impairment of human polymorphonuclear leukocyte chemotaxis by 2,5-hexanedione.
Respiratory-phase-related coding of olfactory information in the olfactory bulb of awake freely-breathing rabbits.
Methodological investigations on the determination of n-hexane metabolites in urine.
Analysis of n-hexane, 2-hexanone, 2,5-hexanedione, and related chemicals by capillary gas chromatography and high-performance liquid chromatography.
Inhalation of isopropanol: induction of activating and deactivating enzymes in rat kidney and liver. Increased microsomal metabolism of n-hexane.
Inhalation of butanols: changes in the cytochrome P-450 enzyme system.
Selective inhibition by chloramphenicol of cytochrome P-450 isozymes in rat lung and liver involved in the hydroxylation of n-hexane.
In vitro effect of n-hexane and its metabolites on selected enzymes in glycolysis, pentose phosphate pathway and citric acid cycle.
Increased microsomal metabolism of n-hexane in rat kidney and liver after inhalation of isopropanol.
Changes of n-hexane neurotoxicity and its urinary metabolites by long-term co-exposure with MEK or toluene.
Production of Methyl Ketones from Secondary Alcohols by Cell Suspensions of C(2) to C(4)n-Alkane-Grown Bacteria.
Ultrastructural studies of the dying-back process. VI. Examination of nerve fibers undergoing giant axonal degeneration in organotypic culture.
Position specificity in n-hexane hydroxylation by two forms of cytochrome P-450 in rat liver microsomes.
Xylene induces a cytochrome P-450 isozyme in rat liver similar to the major isozyme induced by phenobarbital.
A study on biological monitoring of n-hexane exposure.
Changes of n-hexane metabolites in urine of rats exposed to various concentrations of n-hexane and to its mixture with toluene or MEK.
Urinary excretion of n-hexane metabolites. A comparative study in rat, rabbit and monkey.
[An experimental study on the neurotoxicity of 2-octanone and 2-hexanol, a metabolite of n-hexane].
Purification and characterization of a nicotinamide adenine dinucleotide-dependent secondary alcohol dehydrogenase from Candida boidinii.
Neurotoxic metabolites of "commercial hexane" in the urine of shoe factory workers.
Experimental neurotoxicity and urinary metabolites of the C5-C7 aliphatic hydrocarbons used as glue solvents in shoe manufacture.
Regio-selectivity of purified forms of rabbit liver microsomal cytochrome P-450 in the metabolism of benzo(a)pyrene, n-hexane and 7-ethoxyresorufin.
Urinary excretion of the metabolites of n-hexane and its isomers during occupational exposure.
Measurement of the urinary metabolites of N-hexane, cyclohexane and their isomers by gas chromatography.
Regulation of primary alkylsulfatase induction in Pseudomonas C12B: concentration-dependent stimulation-inhibition by exogenous UTP and sodium acetate and inhibition by 1-hexanol.
Microbial Oxidation of Gaseous Hydrocarbons: Production of Secondary Alcohols from Corresponding n-Alkanes by Methane-Utilizing Bacteria.
Microbial production of methyl ketones. Purification and properties of a secondary alcohol dehydrogenase from yeast.
Oxidation of secondary alcohols to methyl ketones by yeasts.
Biotransformation of n-hexane and methyl n-butyl ketone in guinea pigs and mice.
The effect of 2-hexanone and 2-hexanone metabolites on pupillomotor activity and growth.
Toxicity and metabolism of methyl n-butyl ketone.
Identification and quantitative analysis of the volatile substances emitted by maturing cotton in the field.

Other Information

(IUPAC):	Atomic Weights of the Elements 2011 (pdf)
Videos:	The Periodic Table of Videos
tgsc:	Atomic Weights use for this web site
(IUPAC):	Periodic Table of the Elements
CHEMBL:	View
HMDB (The Human Metabolome Database):	Search
FooDB:	FDB004514
Export Tariff Code:	2905.19.9090
Typical G.C.
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View
Wikipedia:	View

Suppliers

Beijing Lys Chemicals	CJ Latta & Associates
Kingchem Laboratories	Nagar Haveli Perfumes & Aromatics
Parchem	Penta International
Sigma-Aldrich	TCI AMERICA
WholeChem	Beijing Lys Chemicals Co, LTD.
CJ Latta & Associates, LLC	Penta International Corporation
WholeChem, LLC

PhysChem Properties

Material listed in food chemical codex	No
Molecular weight	102.17678070068
Specific gravity	@ 20 °C
Pounds per Gallon	6.781 to 6.798
Refractive Index	1.414 to 1.416 @ 20 °C
Boiling Point	136 to 139°C @ 760 mm Hg
Vapor Pressure	2.634 mmHg @ 25 °C
Flash Point TCC Value	46.11 °C TCC
logP (o/w)	1.702 est
Solubility
alcohol	Yes
water, 1.171e+004 mg/L @ 25 °C (est)	Yes
water	No

Organoleptic Properties

Odor Type: Winey
chemical, winey, fruity, fatty, terpenic, cauliflower
General comment	At 1.00 % in dipropylene glycol. chemical winey fruity fatty terpenic cauliflower

Occurrences

Potential Uses

Applications	flavor and fragrance agents
Odor purposes	Herbal, Lavender, Pineapple
Cosmetic purposes	Perfuming agents

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 10 - Flammable. R 22 - Harmful if swallowed. R 36/37/38 - Irritating to eyes, respiratory system, and skin. S 02 - Keep out of the reach of children. S 16 - Keep away from sources of ignition - No Smoking. S 20/21 - When using do not eat, drink or smoke. S 24/25 - Avoid contact with skin and eyes. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 36 - Wear suitable protective clothing.

Hazards identification

Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements

Pictogram

Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for 2-hexanol usage levels up to:
	0.8000 % in the fragrance concentrate.