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dextro,laevo-neomenthol

Dextro,laevo-neomenthol is a cyclohexanol derivative with mentholic odor, used predominantly as a flavor and fragrance agent in various essential oils.

General Material Description

Dextro,laevo-neomenthol, chemically known as 5-methyl-2-(propan-2-yl)cyclohexanol, is a bicyclic cyclohexanol compound with the molecular formula C10H20O and a molecular weight of approximately 156.27 g/mol. It is an isomer related to menthols, exhibiting a characteristic mentholic, cooling minty odor. The material appears as a colorless liquid, often used in flavor and fragrance formulations. It is also known by synonyms including (2R,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol and D,L-neo menthol. The compound is documented in major chemical databases such as PubChem, reflecting its well-characterized chemical identity. Sourced primarily from natural essential oils like peppermint and pennyroyal oils, it can also be synthetically produced. Due to its olfactory properties, it finds use in perfuming agents and flavor components.

Occurrence, Applicability & Potential Uses

Dextro,laevo-neomenthol is naturally present in diverse essential oils, including those from cornmint, pennyroyal, peppermint, and tansy plants. Its concentration varies by source, for instance, comprising up to around 3.7% in Mongolian peppermint oil and between 0.1% to 4.2% in various pennyroyal oils from different regions. The compound's minty and cooling sensory attributes support its application in flavor and fragrance industries. It is used as a flavor agent in food products and as a perfuming substance in cosmetics. The material complies with industry standards such as the IFRA Code of Practice (Global), which governs fragrance ingredient usage to ensure safety in consumer goods. Its role as a functional aroma compound enhances sensory profiles related to freshness and cooling.

Physico-Chemical Properties Summary

Physicochemically, dextro,laevo-neomenthol exhibits a moderate molecular weight with a formula of C10H20O. At atmospheric pressure (760 mm Hg), it boils between 214 and 216°C, indicating relative thermal stability suitable for fragrance applications. It has a low vapor pressure of approximately 0.032 mmHg at 25°C, which influences its volatility and evaporation rate in formulations. The flash point is about 93°C (200°F), reflecting moderate flammability risk under controlled conditions. Solubility profiles show it dissolves in alcohols and sparingly in water (approximately 434.5 mg/L at 25°C estimated), dictating solvent choices in product formulations. An estimated logP of 3.216 indicates a moderately lipophilic nature, which affects its distribution in oil-based versus aqueous phases. These properties facilitate its incorporation into diverse flavor and fragrance matrices while maintaining scent integrity and compound stability.

FAQ

What is dextro,laevo-neomenthol and what are its key characteristics?
Dextro,laevo-neomenthol is a cyclohexanol derivative with the molecular formula C10H20O, chemically described as 5-methyl-2-(propan-2-yl)cyclohexanol. It has a distinctive mentholic and cooling minty odor, making it valuable in flavor and fragrance formulations. The compound appears as a colorless liquid with moderate volatility and is chemically related to menthols, but differs structurally and functionally in its sensory profile.
Where does dextro,laevo-neomenthol occur naturally, and how is it used industrially?
This compound occurs naturally in various essential oils such as peppermint oil, pennyroyal oil, cornmint oil, and tansy oil with concentrations ranging from around 0.1% to over 3% depending on the source and region. Industrially, it serves as a flavoring agent and perfuming ingredient in cosmetics, where its mentholic odor contributes to cooling and fresh scent profiles. The compound is incorporated into products following guidelines like the IFRA Code of Practice to control safe usage levels.
What safety and regulatory information should be considered for dextro,laevo-neomenthol?
Dextro,laevo-neomenthol is classified as having no significant hazards under OSHA's Hazard Communication Standard (29 CFR 1910). Toxicity data indicate an oral mouse LD50 of 4000 mg/kg, suggesting low acute toxicity. It is subject to fragrance industry regulations, including IFRA standards (Global), ensuring its safe application in consumer products. Safety assessments are accessible through resources such as RIFM and EPA databases, with no major precautionary statements required under standard handling conditions.

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Literature & References

5-methyl-2-(propan-2-yl)cyclohexanol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:491-01-0
Pubchem (cid):19243
Pubchem (sid):134984254
Pherobase:View
(2R,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:3623-51-6
Pubchem (cid):19243
Pubchem (cas):3623-51-6
Publications by PubMed
[On the assay of DL-menthol for contamination by DL-neomenthol. 2. Report on the menthol monography in a new German pharmacopoeia].
Acaricidal activity of constituents derived from peppermint oil against Tyrophagus putrescentiae.
Genetic variability, character association, and path analysis for economic traits in menthofuran rich half-sib seed progeny of Mentha piperita L.
Identification of genetic markers linked to anthracnose resistance in sorghum using association analysis.
Immunocytochemical localization of short-chain family reductases involved in menthol biosynthesis in peppermint.
The Arabidopsis short-chain dehydrogenase/reductase 3, an abscisic acid deficient 2 homolog, is involved in plant defense responses but not in ABA biosynthesis.
Stereoselective effects of monoterpenes on the microviscosity and curvature of model membranes assessed by DPH steady-state fluorescence anisotropy and light scattering analysis.
Chemical diversity of Ziziphora clinopodioides: composition of the essential oil of Z. clinopodioides from Tajikistan.
Peppermint oil decreases the production of virulence-associated exoproteins by Staphylococcus aureus.
Intraspecific variability of the essential oil of Ziziphora clinopodioides ssp. rigida from Iran.
Chirality recognition in menthol and neomenthol: preference for homoconfigurational aggregation.
Molecular cloning and characterization of a broad substrate terpenoid oxidoreductase from Artemisia annua.
Evolution of morphine biosynthesis in opium poppy.
Headspace solid-phase microextraction-gas chromatography-mass spectrometry determination of the characteristic flavourings menthone, isomenthone, neomenthol and menthol in serum samples with and without enzymatic cleavage to validate post-offence alcohol drinking claims.
Terpene conjugates of diaminedichloridoplatinum(II) complexes: antiproliferative effects in HL-60 leukemia, 518A2 melanoma, and HT-29 colon cancer cells.
A role for a menthone reductase in resistance against microbial pathogens in plants.
Sedative effect of monoterpene alcohols in mice: a preliminary screening.
Volatile terpenoids of endophyte-free and infected peppermint (Mentha piperita L.): chemical partitioning of a symbiosis.
Biotransformation of (-)-menthone by human liver microsomes.
Monoterpene metabolism. Cloning, expression, and characterization of menthone reductases from peppermint.
Effect of Mentha x piperita essential oil and monoterpenes on cucumber root membrane potential.
Effect of melting point of chiral terpenes on human stratum corneum uptake.
Monoterpene composition of essential oil from peppermint (Mentha x piperita L.) with regard to leaf position using solid-phase microextraction and gas chromatography/mass spectrometry analysis.
Influence of drug lipophilicity on terpenes as transdermal penetration enhancers.
Effect of l-menthol on laryngeal receptors.
The effects of menthol isomers on nasal sensation of airflow.
Biotransformation by divison-arrested and immobilized plant cells: bioconversion of monoterpenes by gamma-irradiated suspended and entrapped cells of mentha and Nicotiana.
Metabolism of Monoterpenes : Evidence for the Function of Monoterpene Catabolism in Peppermint (Mentha piperita) Rhizomes.
Metabolism of Monoterpenes : Early Steps in the Metabolism of d-Neomenthyl-beta-d-Glucoside in Peppermint (Mentha piperita) Rhizomes.
Biotransformation by plant cells immobilized in cross-linked polyacrylamide-hydrazide.
Metabolism of Monoterpenes: Conversion of l-Menthone to l-Menthol and d-Neomenthol by Stereospecific Dehydrogenases from Peppermint (Mentha piperita) Leaves.
Demonstration of the Intercellular Compartmentation of l-Menthone Metabolism in Peppermint (Mentha piperita) Leaves.
Biotransformation of monoterpenes by mentha cell lines: conversion of menthone to neomenthol.
Metabolism of Monoterpenes : EVIDENCE FOR COMPARTMENTATION OF l-MENTHONE METABOLISM IN PEPPERMINT (MENTHA PIPERITA) LEAVES.
Metabolism of Monoterpenes: Demonstration of (+)-Neomenthyl-beta-d-Glucoside as a Major Metabolite of (-)-Menthone in Peppermint (Mentha Piperita).
[On the assay of DL-menthol for contamination by DL-neomenthol. 2. Report on the menthol monography in a new German pharmacopoeia].

General Material Information

Preferred name dextro,laevo-neomenthol
Trivial Name 5-methyl-2-(propan-2-yl)cyclohexanol
Short Description cyclohexanol, 5-methyl-2-(1-methylethyl)-, (2R,5R)-
Formula C10 H20 O
CAS Number 491-01-0
CAS Number 3623-51-6
Deleted CAS Number 3623-51-6
ECHA Number 207-723-2
FDA UNII 89S3KO7RR9
xLogP3-AA 3.00 (est)
NMR Predictor External link
Synonyms
  • cyclohexanol, 5-methyl-2-(1-methylethyl)-, (2R,5R)-
  • (±)-neo menthol
  • D,L-neo menthol
  • trans-1,3-cis-1,4-(±)- menthol
  • (2R,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol

Suppliers

Som Extracts

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 156.26860046387
Boiling Point 214 to 216°C @ 760 mm Hg
Vapor Pressure 0.032 mmHg @ 25 °C
Flash Point TCC Value 93.33 °C TCC
logP (o/w) 3.216 est
Solubility
alcohol Yes
water, 434.5 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Mentholic
mentholic, cooling, minty
General comment At 10.00 % in dipropylene glycol. mentholic cooling minty

Occurrences

Safety Information

Safety information

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:
oral-mouse LD50 4000 mg/kg
Quarterly Journal of Pharmacy & Pharmacology. Vol. 5, Pg. 233, 1932.

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

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):491-01-0
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :19243
National Institute of Allergy and Infectious Diseases:Data
5-methyl-2-(propan-2-yl)cyclohexanol
Chemidplus:0003623516
(2R,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol