(+)-Neomenthol
[CAS# 2216-52-6]

Identification

• Classification: Organic raw materials >> Alcohols, phenols, phenolic compounds and derivatives
• Name: (+)-Neomenthol
• Synonyms: (1S,2S,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol
• Molecular Formula: C₁₀H₂₀O
• Molecular Weight: 156.27
• CAS Registry Number: 2216-52-6
• EC Number: 218-691-4
• SMILES: C[C@@H]1CC[C@H]([C@H](C1)O)C(C)C

Properties

• Density: 0.899 g/mL (Expl.)
• Melting point: -22 ºC (Expl.)
• Boiling point: 215.4±8.0 ºC 760 mmHg (Calc.)^*, 238.6 ºC (Expl.)
• Flash point: 93.3 ºC (Calc.)^*, 83 ºC (Expl.)
• Index of refraction: 1.457 (Calc.)^*, 1.461 (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

moderate lipophilicity (log P ~ 3.4), which influences its solubility and permeability properties.

The most widespread applications of (+)-Neomenthol exploit its sensory profile — notably its cooling, minty odor and flavor. It is used as a flavoring agent and fragrance ingredient in food products, chewing gum, confectionery, beverages, mouthwash, and oral hygiene products. ([CymitQuimica][3]) In cosmetics and topical formulations, its cooling sensation — similar to but distinct from that of menthol — is valued in creams, ointments, lotions, and personal-care products.

More recent research has expanded interest in the biological activity of (+)-Neomenthol. One study reported that neomenthol exhibits antiproliferative effects against human epidermoid carcinoma (A431) cells, with an IC₅₀ in the low micromolar range. The mechanism appears to involve inhibition of hyaluronidase activity and interference with tubulin polymerization, leading to cell-cycle arrest at G2/M and increased sub-diploid cell populations. In a mouse tumor model, neomenthol reduced tumor formation significantly at a tolerated dose. ([PubMed][5]) These data suggest that beyond fragrance and flavor, neomenthol (or derivatives) may have potential as scaffolds for anticancer or other therapeutic agents — though more comprehensive studies would be needed.

Chemically, as a saturated cyclohexanol derivative with a chiral center, (+)-Neomenthol can participate in standard reactions for alcohols — e.g., esterification, etherification, oxidation to ketones, or substitution — though most applications leverage its intact structure because of its sensory and biological activity. Its relatively high lipophilicity and volatility also facilitate its incorporation into lipophilic formulations or volatile fragrance blends.

Overall, (+)-Neomenthol is a naturally occurring (and synthetically accessible) monoterpenoid alcohol whose minty aroma, cooling sensation, and moderate pharmacological activity underpin its broad use in flavor, fragrance, cosmetic, and emerging biomedical applications. Its simple structure and stereochemistry also make it a convenient model compound in research on chiral terpenoids and their biological effects.

References

2023. The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata). Zenodo.
DOI: 10.5281/zenodo.5794106

2011. Transcript and metabolite analysis in Trincadeira cultivar reveals novel information regarding the dynamics of grape ripening. BMC Plant Biology, 11(1).
DOI: 10.1186/1471-2229-11-149

2009. Evolution of morphine biosynthesis in opium poppy. Phytochemistry, 70(15-16).
DOI: 10.1016/j.phytochem.2009.07.006