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endo-1,2,3,3-tetramethyl bicyclo(2.2.1)heptan-2-ol

endo-1,2,3,3-tetramethyl bicyclo(2.2.1)heptan-2-ol is a bicyclic alcohol used as a fragrance agent noted for its stable vegetal and green mossy odor characteristics.
Chemical Structure

General Material Description

endo-1,2,3,3-tetramethyl bicyclo(2.2.1)heptan-2-ol is a bicyclic tertiary alcohol known also as methyl fenchol and humus ether (Takasago). It contains eleven carbon atoms and one oxygen atom with the molecular formula C11H20O and a molecular weight of approximately 168.28 g/mol. This compound exhibits a medium-strength, vegetal, green mossy odor which makes it valued in the flavor and fragrance industry. The bicyclo[2.2.1]heptane skeleton provides a unique structural framework contributing to its olfactory profile. It is synthetically derived and can be linked to its PubChem entry (CID 119965) for further chemical information. Its sources are chiefly synthetic, aiming to replicate natural mossy nuances in perfumery formulations.

Occurrence, Applicability & Potential Uses

endo-1,2,3,3-tetramethyl bicyclo(2.2.1)heptan-2-ol does not naturally occur in significant biological systems but is manufactured for its valued scent properties. It finds applications primarily as a fragrance ingredient in perfume compositions, where it enhances naturalness and diffusion especially in floral and green accords, even at trace levels. Due to its stable and distinctive green-mossy odor, it is broadly employed in high-quality perfuming agents. The IFRA (Global) standard has issued usage level recommendations that restrict its concentration to a maximum of 0.1% in fragrance concentrates to ensure consumer safety and regulatory compliance. It is not recommended or used for flavor applications.

Physico-Chemical Properties Summary

This compound has a moderate boiling range between 208 and 209°C at standard atmospheric pressure. Its estimated partition coefficient (logP) of around 2.9 indicates lipophilic characteristics suitable for fragrance diffusion and moderate volatility. The vapor pressure is low at 0.049 mmHg at 25°C, supporting its substantivity in formulations with more than 24 hours longevity at full concentration. solubility data suggest it dissolves well in alcohol solvents but has limited solubility in water, consistent with its hydrophobic bicyclic structure. The flash point is approximately 82°C (182°F), indicating relatively safe handling under typical conditions used in perfumery manufacture. These physicochemical traits directly influence its formulation stability, scent release, and compatibility with other ingredients.

FAQ

What is endo-1,2,3,3-tetramethyl bicyclo(2.2.1)heptan-2-ol and what are its key aroma characteristics?
endo-1,2,3,3-tetramethyl bicyclo(2.2.1)heptan-2-ol is a bicyclic tertiary alcohol widely used in the fragrance industry. It is known for a medium-strength, vegetal, green, and mossy odor that provides freshness and naturalness to perfume compositions. The compound's stability and scent diffusion make it a valuable ingredient in green and floral fragrance accords.
How is endo-1,2,3,3-tetramethyl bicyclo(2.2.1)heptan-2-ol typically used and in what products?
This substance is predominantly applied as a perfuming agent in fragrances. It enhances the green and mossy aroma notes, contributing to the complexity and natural character of perfumes and scented products. It is used at trace to low concentrations, typically below 0.1% in fragrance concentrates, to maintain olfactory balance without overwhelming. It is not used as a flavor additive.
What safety regulations govern the use of endo-1,2,3,3-tetramethyl bicyclo(2.2.1)heptan-2-ol in fragrance formulations?
The International Fragrance Association (IFRA, Global) sets guidelines limiting the compound's use to a maximum of 0.1% in fragrance concentrates to ensure safe consumer exposure. No significant hazard classifications have been identified under OSHA's Globally Harmonized System. Safety data indicate no known requirements for precautionary labeling or special handling beyond standard industrial hygiene practices.

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

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Other Information

General Material Information

Preferred name endo-1,2,3,3-tetramethyl bicyclo(2.2.1)heptan-2-ol
Trivial Name rel-(1R,2R,4S)-1,2,3,3-Tetramethylbicyclo[2.2.1]heptan-2-ol
Short Description humus ether (Takasago)
Formula C11 H20 O
CAS Number 28462-85-3
ECHA Number 249-036-0
FDA UNII Search
xLogP3-AA 2.70 (est)
NMR Predictor External link
Synonyms
  • bicyclo(2.2.1)heptan-2-ol, 1,2,3,3-tetramethyl-, (1R,2R,4S)-rel-
  • bicyclo(2.2.1)heptan-2-ol, 1,2,3,3-tetramethyl-, endo-
  • humus ether (Takasago)
  • (1,2,3,3-tetramethyl bicyclo(2.2.1)heptan-2-ol
  • endo-1,2,3,3-tetramethylbicyclo(2.2.1)heptan-2-ol
  • (1R,3R,4R)-2,2,3,4-tetramethylbicyclo[2.2.1]heptan-3-ol
  • Bicyclo[2.2.1]heptan-2-ol, 1,2,3,3-tetramethyl-, (1R,2R,4S)-rel-
  • Bicyclo[2.2.1]heptan-2-ol, 1,2,3,3-tetramethyl-, endo-
  • rel-(1R,2R,4S)-1,2,3,3-Tetramethylbicyclo[2.2.1]heptan-2-ol
  • Methyl fenchol

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 168.27960205078
Boiling Point 208 to 209°C @ 760 mm Hg
Vapor Pressure 0.049 mmHg @ 25 °C
Flash Point TCC Value 83.5 °C TCC
logP (o/w) 2.931 est
Solubility
alcohol Yes
water, 305.1 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Vegetable
vegetable, green, mossy
Odor strength medium
Substantivity > 24 hour(s) at 100.00 %
General comment At 100.00 %. vegetable green mossy
A very versatile ingredient of excellent stability that provides or enhances naturalness and diffusion in floral and green fragrances at trace levels. Vegetal, Green, Mossy

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:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
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 endo-1,2,3,3-tetramethyl bicyclo(2.2.1)heptan-2-ol usage levels up to:
0.1000 % in the fragrance concentrate.
Recommendation for endo-1,2,3,3-tetramethyl bicyclo(2.2.1)heptan-2-ol flavor usage levels up to:
not for flavor use.

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):28462-85-3
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :119965
National Institute of Allergy and Infectious Diseases:Data
(1R,3R,4R)-2,2,3,4-tetramethylbicyclo[2.2.1]heptan-3-ol
Chemidplus:0028462853