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cyclohexanol

Chemical Structure

General Material Information

Preferred name cyclohexanol
Trivial Name Cyclohexanol
Short Description hydroxycyclohexane
Formula C6 H12 O
CAS Number 108-93-0
Flavis Number 2.07
ECHA Number 203-630-6
FDA UNII 8E7S519M3P
Nikkaji Number J2.871A
Beilstein Number 0906744
MDL MFCD00003855
COE Number 2138
xLogP3-AA 1.20 (est)
Bio Activity Summary External link
NMR Predictor External link
Synonyms
  • adronal
  • adronol
  • 1-cyclohexanol
  • cyclohexanol w/methanol
  • cyclohexyl alcohol
  • hexahydrophenol
  • hexalin
  • hydralin
  • hydrophenol
  • hydroxycyclohexane
  • naxol
  • Anol
  • Phenol, hexahydro-
  • Hexalin (alcohol)
  • 1-Cyclohexanol
  • NSC 403656
  • NSC 54711

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

cyclohexanol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:108-93-0
Pubchem (cid):7966
Pubchem (sid):134973337
Pherobase:View
Publications by PubMed
Migration of odorous compounds from adhesives used in market samples of food packaging materials by chromatography olfactometry and mass spectrometry (GC-O-MS).
Isolation, purification and identification of nine chemical compounds from Flammulina velutipes fruiting bodies.
Identification of raloxifene as a novel CB2 inverse agonist.
Opioids in the perifornical lateral hypothalamus suppress ethanol drinking.
Preparation and evaluation of poly(4-vinylphenylboronic acid-co-pentaerythritol triacrylate) monolithic column for capillary liquid chromatography of small molecules and proteins.
Chronic cannabinoid treatment during young adulthood induces sex-specific behavioural deficits in maternally separated rats.
A novel toxic alkaloid from poison hemlock (Conium maculatum L., Apiaceae): identification, synthesis and antinociceptive activity.
Dietary conditions and highly palatable food access alter rat cannabinoid receptor expression and binding density.
Glycosidic conjugates of C13 norisoprenoids, monoterpenoids, and cucurbates in Boronia megastigma (Nees).
Structural and pharmacological analysis of O-2050, a putative neutral cannabinoid CB(1) receptor antagonist.
Chronic Δ⁹-tetrahydrocannabinol treatment in rhesus monkeys: differential tolerance and cross-tolerance among cannabinoids.
Electrochromatographic characterization of methacrylate ester-based monolith and capillary electrochromatography separation of flavonoids.
The peptide hemopressin acts through CB1 cannabinoid receptors to reduce food intake in rats and mice.
Preparation of a neutral porous monolith and its evaluation in pressurized capillary electrochromatography with neutral and charged solutes.
Opioids in the hypothalamic paraventricular nucleus stimulate ethanol intake.
Preparation and evaluation of the highly cross-linked poly(1-hexadecane-co-trimethylolpropane trimethacrylate) monolithic column for capillary electrochromatography.
Opioids in the nucleus accumbens stimulate ethanol intake.
Central cannabinoid signaling mediating food intake: a pharmacological-challenge magnetic resonance imaging and functional histology study in rat.
Determination of tetracyclines in food samples by molecularly imprinted monolithic column coupling with high performance liquid chromatography.
Fragrance material review on 1-methyl-4-(1-methylvinyl)cyclohexyl acetate.
Fragrance material review on cyclohexyl acetate.
Fragrance material review on 1-methyl-2-(1-methylpropyl) cyclohexyl acetate.
Fragrance material review on dihydrocarveol (R,R,R).
Fragrance material review on dihydrocarveol.
Pharmacological evaluation of LH-21, a newly discovered molecule that binds to cannabinoid CB1 receptor.
The effects of antipsychotics on the density of cannabinoid receptors in the dorsal vagal complex of rats: implications for olanzapine-induced weight gain.
Cannabinoid agonists differentially substitute for the discriminative stimulus effects of Delta(9)-tetrahydrocannabinol in C57BL/6J mice.
PSNCBAM-1, a novel allosteric antagonist at cannabinoid CB1 receptors with hypophagic effects in rats.
Antiobesity efficacy of a novel cannabinoid-1 receptor inverse agonist, N-[(1S,2S)-3-(4-chlorophenyl)-2-(3-cyanophenyl)-1-methylpropyl]-2-methyl-2-[[5-(trifluoromethyl)pyridin-2-yl]oxy]propanamide (MK-0364), in rodents.
Interactions between endocannabinoids and stress-induced decreased sensitivity to natural reward.
Antiobesity effects of the novel in vivo neutral cannabinoid receptor antagonist 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-3-hexyl-1H-1,2,4-triazole--LH 21.
Novel approach to the detection and quantification of phenolic compounds in olive oil based on 31P nuclear magnetic resonance spectroscopy.
Analyses of phenolic compounds by microemulsion electrokinetic chromatography.
Cannabinoids augment the release of neuropeptide Y in the rat hypothalamus.
Structure-function analysis of the vanillin molecule and its antifungal properties.
Discriminative stimulus effects of the structurally novel cannabinoid CB1/CB2 receptor partial agonist BAY 59-3074 in the rat.
Effects of the kappa opioid agonist U50,488 and the kappa opioid antagonist nor-binaltorphimine on choice between cocaine and food in rhesus monkeys.
Partial agonist-like profile of the cannabinoid receptor antagonist SR141716A in a food-reinforced operant paradigm.
Behavioral effects of cannabinoids show differential sensitivity to cannabinoid receptor blockade and tolerance development.
Cannabinoid agonist, CP 55,940, facilitates intake of palatable foods when injected into the hindbrain.
In vivo studies on the metabolism of the monoterpene pulegone in humans using the metabolism of ingestion-correlated amounts (MICA) approach: explanation for the toxicity differences between (S)-(-)- and (R)-(+)-pulegone.
Intrinsic activity estimation of cannabinoid CB1 receptor ligands in a drug discrimination paradigm.
Chronic treatment with CP 55,940 during the peri-adolescent period differentially affects the behavioural responses of male and female rats in adulthood.
Discriminative stimulus effects of BAY 38-7271, a novel cannabinoid receptor agonist.
Delta opioid antagonist effects of buprenorphine in rhesus monkeys.
Kappa opioid antagonist effects of the novel kappa antagonist 5'-guanidinonaltrindole (GNTI) in an assay of schedule-controlled behavior in rhesus monkeys.
Stimulation of voluntary ethanol intake by cannabinoid receptor agonists in ethanol-preferring sP rats.
Estimation of trace amounts of benzene in solvent-extracted vegetable oils and oil seed cakes.
Effects of kappa opioids on cocaine self-administration by rhesus monkeys.
Applications of High-Temperature Aqueous Media for Synthetic Organic Reactions.
Effects of the cannabinoid CB1 receptor antagonist SR141716A on the behavior of pigeons and rats.
A specific and sensitive method for the determination of linamarin in Urine.
The involvement of the sympathetic nervous system in meal-induced thermogenesis in mice.
Isolation and characterization of an anaerobic dehydrodivanillin-degrading bacterium.

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
FDA Indirect Additives used in Food Contact Substances:View
CHEBI:View
CHEMBL:View
Metabolomics Database:Search
UM BBD:Search
KEGG (GenomeNet):C00854
HMDB (The Human Metabolome Database):Search
FooDB:FDB003415
YMDB (Yeast Metabolome Database):YMDB01398
Export Tariff Code:2906.12.0000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
Formulations/Preparations:
•grade: technical (contains freezing inhibitor) •commercial products: technical and high-grade •some cyclohexanol is shipped with 2.25% methanol as antifreeze. •ka oil used for adipic acid production is 65% cyclohexanol

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 100.16084289551
Specific gravity @ 25 °C
Pounds per Gallon 7.838 to 7.888
Refractive Index 1.462 to 1.468 @ 20 °C
Vapor Pressure 0.975 mmHg @ 20 °C
Vapor Density 3.5
Flash Point TCC Value 62.78 °C TCC
logP (o/w) 1.23
Solubility
water, 42000 mg/L @ 10 °C (exp) Yes

Organoleptic Properties

Odor Type: Camphoreous
camphoreous, mentholic, phenolic
General comment At 10.00 % in dipropylene glycol. camphor menthol phenol

Occurrences

Safety Information

Safety information

European information :
Most important hazard(s):
Xn - Harmful.
R 20/22 - Harmful by inhalation and if swallowed.
R 37/38 - Irritating to respiratory system and skin.
S 02 - Keep out of the reach of children.
S 20/21 - When using do not eat, drink or smoke.
S 22 - Do not breath dust.
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 36/37/39 - Wear suitable clothing, gloves and eye/face protection.
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:
gavage-rat LD50 [sex: M] 1750 mg/kg
(Miller & Sherman, 1965)

oral-rat LD50 1550 mg/kg
(Birch, 1978a)

oral-rat LD50 2060 mg/kg
(Bär & Griepentrog, 1967)

oral-rat LD50 [sex: M,F] 1120 mg/kg
(Birch et al., 1981)

oral-rat LD50 2060 mg/kg
Administered as 10 % solution in Tergitol 7.
(Smyth et al., 1946c)

gavage-rabbit LD50 2200 - 2600 mg/kg
Minimum lethal dose.
(Treon et al., 1943)

parenteral-frog LDLo 1914 mg/kg
CARDIAC: OTHER CHANGES
Journal of Pharmacology and Experimental Therapeutics. Vol. 24, Pg. 405, 1925.

intramuscular-mouse LD50 1000 mg/kg
Journal of Scientific and Industrial Research, Section C: Biological Sciences. Vol. 21, Pg. 342, 1962.

intraperitoneal-mouse LD50 1352 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1254, 1969.

intravenous-mouse LD50 272 mg/kg
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 135, Pg. 330, 1962.

oral-rabbit LDLo 2200 mg/kg
BEHAVIORAL: GENERAL ANESTHETIC
Journal of Industrial Hygiene and Toxicology. Vol. 25, Pg. 199, 1943.

oral-rat LD50 1400 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
National Technical Information Service. Vol. OTS0538617

Dermal Toxicity:
skin-rabbit LDLo 794 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LIVER: CHANGE IN GALL BLADDER STRUCTURE OR FUNCTION
National Technical Information Service. Vol. OTS0538617

Inhalation Toxicity:
inhalation-human TCLo 75 ppm
SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Journal of Industrial Hygiene and Toxicology. Vol. 25, Pg. 282, 1943.

inhalation-rat LC > 6500 mg/m3/1H
National Technical Information Service. Vol. OTS0572832

Safety in use information

Category:
flavoring agents and cosmetic fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Maximised Survey-derived Daily Intakes (MSDI-EU): 3.70 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 1600 (μg/person/day)
Threshold of Concern:1800 (μg/person/day)
Structure Class: I
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 3.0000015.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 2.0000010.00000
Edible ices, including sherbet and sorbet (03.0): 3.0000015.00000
Processed fruit (04.1): 2.0000010.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 4.0000020.00000
Chewing gum (05.3): --
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 2.0000010.00000
Bakery wares (07.0): 5.0000025.00000
Meat and meat products, including poultry and game (08.0): 1.000005.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 1.000005.00000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 2.0000010.00000
Foodstuffs intended for particular nutritional uses (13.0): 3.0000015.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 2.0000010.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 4.0000020.00000
Ready-to-eat savouries (15.0): 5.0000025.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 2.0000010.00000

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) on a request from the Commission related to Flavouring Group Evaluation 9 (FGE.09): Secondary alicyclic saturated and unsaturated alcohols, ketones and esters containing secondary alicyclic alcohols from chemical group 8 and an ester of a phenol carboxylic acid from chemical group 25
View page or View pdf

Flavouring Group Evaluation 51, (FGE.51)[1] - Consideration of alicyclic ketones and secondary alcohols and related esters evaluated by JECFA (59th meeting) and structurally related to alicyclic ketones, secondary alcohols and related esters evaluated by EFSA in FGE.09 (2004) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf

Flavouring Group Evaluation 9, Revision 1: (FGE.09 Rev1)[1] - Secondary alicyclic saturated and unsaturated alcohols, ketones and esters containing secondary alicyclic alcohols from chemical groups 8 and 30, and an ester of a phenol carboxylic acid from chemical group 25 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf

Flavouring Group Evaluation 9, Revision 2 (FGE.09Rev2): Secondary alicyclic saturated and unsaturated alcohols, ketones and esters containing secondary alicyclic alcohols from chemical group 8 and 30, and an ester of a phenol derivative from chemical group 25
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 9, Revision 3 (FGE.09Rev3): Secondary alicyclic saturated and unsaturated alcohols, ketones and esters containing secondary alicyclic alcohols from chemical group 8 and 30, and an ester of a phenol derivative from chemical group 25
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 9, Revision 4 (FGE.09Rev4): Secondary alicyclic saturated and unsaturated alcohols, ketones and esters containing secondary alicyclic alcohols from chemical group 8 and 30, and an ester of a phenol derivative from chemical group 25
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 9, Revision 5 (FGE.09Rev5): Secondary alicyclic saturated and unsaturated alcohols, ketones and esters containing secondary alicyclic alcohols from chemical group 8 and 30, and an ester of a phenol derivative from chemical group 25
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 9, Revision 6 (FGE.09Rev6): Secondary alicyclic saturated and unsaturated alcohols, ketones and esters containing secondary alicyclic alcohols from chemical group 8 and 30, and an ester of a phenol derivative from chemical group 25
View page or View pdf

EPI System: View
NIOSH International Chemical Safety Cards:search
NIOSH Pocket Guide:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA GENetic TOXicology:Search
EPA Substance Registry Services (TSCA):108-93-0
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :7966
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
cyclohexanol
Chemidplus:0000108930
EPA/NOAA CAMEO:hazardous materials
RTECS:108-93-0