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dextro,laevo-menthol
General Material Information
| Preferred name | dextro,laevo-menthol |
| Trivial Name | (±)-Menthol |
| Short Description | DL-menthol |
| Formula | C10 H20 O |
| CAS Number | 89-78-1 |
| Deleted CAS Number | 15356-70-4 |
| FEMA Number | 2665 |
| Flavis Number | 2.015 |
| FDA UNII | YS08XHA860 |
| Nikkaji Number | J2.129F |
| Beilstein Number | 3194263 |
| MDL | MFCD00001484 |
| COE Number | 63 |
| xLogP3-AA | 3.00 (est) |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| JECFA Food Flavoring | 427 menthol |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 89-78-1 ; MENTHOL |
| Synonyms |
|
US / EU / FDA / JECFA / FEMA / Scholar / Patents
| Google Scholar | Start search |
| Google Books | Start search |
| Google Patents | Start search |
| Perfumer & Flavorists | Start search |
| EU Patents | Start search |
| PubMeb | Start search |
| NCBI | Start search |
Literature & References
| Leffingwell: | Chirality or Article |
| 5-methyl-2-propan-2-ylcyclohexan-1-ol | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 89-78-1 |
| Pubchem (cid): | 1254 |
| Pubchem (sid): | 134972992 |
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 Substances Added to Food (formerly EAFUS): | View |
| CHEBI: | View |
| CHEMBL: | View |
| KEGG (GenomeNet): | D04849 |
| HMDB (The Human Metabolome Database): | HMDB35765 |
| FooDB: | FDB015462 |
| Export Tariff Code: | 2906.11.0000 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
| Formulations/Preparations: •some synthetic menthols are not chemical individuals but...mixtures of various isomers...these are designated...l-menthol, dl-menthol, l-isomenthol, d-isomenthol, dl-isomenthol, l-neomenthol, d-neomenthol, l-neoisomenthol, d-neoisomenthol and dl-neoisomenthol. •when mixed with about equal wt of camphor, chloral hydrate, phenol, or thymol, menthol forms "eutectic" mixt liquifying @ room temp. •menthol, usp drug marketed under generic name. •grades: technical; usp; fcc •synthetic menthol is available as the optically active levo-menthol with a purity of 99.9%. synthetic menthol is also commercially available as the racemic mixture •present in cigarettes and pipe tobacco (0.1-0.45%) shaving creams, pre- and aftershave lotions (0.2-0.3%); toothpastes (0.5%); mouthwashes (1-2%); chewing gums (0.5%); cough drops (0.1%); refreshing towels (1%); rubbing alcohol (1-1.2%); and shampoos (2-0.5%) •mentholatum deep heating rub contains 5.9% menthol; mentholatum ointment, 1.35%; mentholatum deep heating lotion, 6% | |
Suppliers
PhysChem Properties
| Material listed in food chemical codex | Yes |
| Molecular weight | 156.26860046387 |
| Melting Point | 34 to 36°C @ 760 mm Hg |
| Boiling Point | 212 to 216°C @ 760 mm Hg |
| Vapor Pressure | 0.032 mmHg @ 25 °C |
| Flash Point TCC Value | 93.33 °C TCC |
| logP (o/w) | 3.4 |
| Shelf life | 24 months (or longer if stored properly.) |
| Storage notes | Store in cool, dry place in tightly sealed containers, protected from heat and light. |
| Solubility | |
| alcohol | Yes |
| paraffin oil | Yes |
| water, 434.5 mg/L @ 25 °C (est) | Yes |
| water, 456 mg/L @ 25 °C (exp) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Mentholic | |
| peppermint, cooling, woody | |
| Odor strength | medium , recommend smelling in a 10.00 % solution or less |
| Substantivity | 32 hour(s) at 100.00 % |
| General comment | At 10.00 % in dipropylene glycol. peppermint cool woody |
| Flavor Type: Cooling | |
| cooling, mentholic, minty | |
| General comment | Cooling mentholic minty |
| Useful in: mint. | Minty-cooling |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Betel, Citrus, Herbal, Mint, Pennyroyal, Peppermint, Rose, Spearmint, Tobacco, Wintergreen |
| Flavoring purposes | Cream ice cream, Pennyroyal |
| Cosmetic purposes | Perfuming agents |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 37/38 - Irritating to respiratory system and skin. R 41 - Risk of serious damage to eyes. S 02 - Keep out of the reach of children. 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 37/39 - Wear suitable gloves and eye/face protection. | |
| Hazards identification | |
| Classification of the substance or mixture | |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) | |
| Skin irritation (Category 2), H315 Serious eye damage (Category 1), H318 Specific target organ toxicity - single exposure (Category 3), Respiratory system, H335 | |
| GHS Label elements, including precautionary statements | |
| Pictogram |   |
| Signal word | Danger |
| Hazard statement(s) | |
| H315 - Causes skin irritation H318 - Causes serious eye damage H335 - May cause respiratory irritation | |
| Precautionary statement(s) | |
| P261 - Avoid breathing dust/fume/gas/mist/vapours/spray. P264 - Wash skin thouroughly after handling. P271 - Use only outdoors or in a well-ventilated area. P280 - Wear protective gloves/protective clothing/eye protection/face protection. P302 + P352 - IF ON SKIN: wash with plenty of soap and water. P304 + P340 - IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. P305 + P351 + P338 - IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P310 - Immediately call a POISON CENTER or doctor/physician. P332 + P313 - IF SKIN irritation occurs: Get medical advice/attention. P362 - Take off contaminated clothing and wash before reuse. P403 + P233 - Store in a well-ventilated place. Keep container tightly closed. P405 - Store locked up. P501 - Dispose of contents/ container to an approved waste disposal plant. | |
| Oral/Parenteral Toxicity: | |
| gavage-mouse LD50 [sex: M] 2652 mg/kg (Food & Drug Research LaboratoriesInc., 1975a) gavage-mouse LD50 [sex: M] 4384 mg/kg (Food & Drug Research Laboratories Inc, 1975a) gavage-mouse LD50 3100 mg/kg (Wokes, 1932) gavage-rat LD50 [sex: M,F] 3180 mg/kg (Jenner et al., 1964) intravenous-cat LDLo 37 mg/kg Archives Internationales de Pharmacodynamie et de Therapie. Vol. 63, Pg. 43, 1939. oral-cat LDLo 1500 mg/kg "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935. intraperitoneal-mouse LDLo 1800 mg/kg Archives Internationales de Pharmacodynamie et de Therapie. Vol. 63, Pg. 43, 1939. intramuscular-rat LD50 10000 mg/kg Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 222, Pg. 244, 1954. oral-rat LD50 3180 mg/kg BEHAVIORAL: ATAXIA Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964. intraperitoneal-rat LDLo 1500 mg/kg BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BEHAVIORAL: SLEEP BEHAVIORAL: MUSCLE WEAKNESS Annales Pharmaceutiques Francaises. Vol. 10, Pg. 481, 1952. | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavor and fragrance agents | |||
| IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice | |||
| maximum skin levels for fine fragrances: | |||
| 0.5200 % and are based on the assumption that the fragrance mixture is used at 20% in a consumer product (IFRA Use Level Survey).(IFRA, 2004) | |||
| Recommendation for dextro,laevo-menthol usage levels up to: | |||
| 8.0000 % in the fragrance concentrate. | |||
| use level in formulae for use in cosmetics: | |||
| 0.2900 % | |||
| Dermal Systemic Exposure in Cosmetic Products: | |||
| 0.0074 mg/kg/day (IFRA, 2004) | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 16000.00 (μg/capita/day) | ||
| Structure Class: | I | ||
| Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS). | |||
| The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library | |||
| publication number: 3 | |||
| Click here to view publication 3 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 130.00000 | |
| beverages(nonalcoholic): | - | 35.00000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | 1100.00000 | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 68.00000 | |
| fruit ices: | - | 68.00000 | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 400.00000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | - | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | - | |
| soups: | - | - | |
| sugar substitutes: | - | - | |
| sweet sauces: | - | - | |
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) related to Flavouring Group Evaluation 18 (FGE.18): Aliphatic, alicyclic and aromatic saturated and unsaturated tertiary alcohols, aromatic tertiary alcohols and their esters from chemical group 6 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 14, Revision 1 (FGE.14Rev1): Phenethyl alcohol, aldehyde, acetals, carboxylic acid and related esters from chemical group 15 and 22 [1] - 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 18, Revision 1 (FGE. 18 Rev1)[1] : Aliphatic, alicyclic and aromatic saturated and unsaturated tertiary alcohols, aromatic tertiary alcohols and their esters from chemical groups 6 and 8 View page or View pdf |
| Flavouring Group Evaluation 43: Thujyl alcohol from chemical group 8 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 90 (FGE.90): Consideration of Aliphatic, acyclic and alicyclic terpenoid tertiary alcohols and structurally related substances evaluated by JECFA (68th meeting)FGE.18Rev1 (2009) 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 |
| Safety and efficacy of secondary alicyclic saturated and unsaturated alcohols, ketones, ketals and esters with ketals containing alicyclic alcohols or ketones and esters containing secondary alicyclic alcohols from chemical group 8 when used as flavourings for all animal species View page or View pdf |
| EPI System: View |
| Chemical Carcinogenesis Research Information System:Search |
| Carcinogenic Potency Database:Search |
| EPA GENetic TOXicology:Search |
| EPA Substance Registry Services (TSCA):89-78-1 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :1254 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:2 |
| 5-methyl-2-propan-2-ylcyclohexan-1-ol |
| Chemidplus:0000089781 |
| EPA/NOAA CAMEO:hazardous materials |
| RTECS:OT0350000 for cas# 89-78-1 |