We have found 46589 results matching your criteria.
Please wait while we search...

laevo-menthyl acetate

Laevo-menthyl acetate is a naturally derived compound with a medium-strength mentholic and minty aroma used extensively in flavors and fragrances.
Chemical Structure

General Material Description

Laevo-menthyl acetate is an ester compound typically found as the L-isomer of menthyl acetate (PubChem). It is a colorless to pale yellow liquid possessing a characteristic cooling mentholic and minty aroma profile. Commonly listed under various synonyms such as (-)-menthyl acetate and L-acetic acid p-menth-3-yl ester, it is naturally present in essential oils from plants like peppermint, spearmint, and eucalyptus. Its sensory attributes combine minty, herbal, and slightly fruity notes, making it valuable in flavoring and fragrance applications. The compound is typically sourced through extraction from natural oils or synthesized for use in consumer products.

Occurrence, Applicability & Potential Uses

Laevo-menthyl acetate occurs naturally in a variety of botanical sources including peppermint, spearmint, eucalyptus oil, cornmint, lemon balm, mango fruit, raspberry, and buchu oil. Its presence contributes to the characteristic minty and fresh sensory qualities of these plants. The compound is widely utilized as a flavor and fragrance agent to impart cooling, minty, and herbal notes in products such as oral care formulations, confectioneries, perfumes, and personal care items. Usage levels are guided by standards such as FEMA (US) and IFRA (Global), which regulate safe incorporation into fragrances and flavors. It is also approved as a Generally Recognized As Safe (GRAS) flavoring substance in many food applications.

Physico-Chemical Properties Summary

Laevo-menthyl acetate (C12H22O2) is characterized by a molecular weight of approximately 198.3 g/mol. The compound is a moderately lipophilic liquid with an estimated logP value of 4.182, indicating good solubility in alcohols, fixed oils, and propylene glycol, along with slight solubility in water measured near 17 mg/L at 25°C. It has a boiling point range near 229 to 230°C at atmospheric pressure, and a specific gravity close to 0.924 to 0.928 at 20°C. The refractive index ranges between 1.445 and 1.448 at 20°C. Its vapor pressure is low, at approximately 0.071 mmHg at 25°C, supporting stability in formulated products. Optical rotation is negative, between −70 and −75 degrees. The compound remains stable and non-discoloring in multiple cosmetic and personal care product bases such as creams, lotions, bath foams, and lipsticks. The flash point is measured around 189°F (87°C), indicating typical handling precautions for flammable liquids.

FAQ

What is laevo-menthyl acetate and what are its main characteristics?
Laevo-menthyl acetate is an ester derived from menthol and acetic acid, primarily recognized for its minty and cooling aroma properties. It is found naturally in essential oils such as peppermint and spearmint and appears as a colorless to pale yellow liquid. The compound has a characteristic mentholic odor with herbal and slightly fruity nuances. Due to these sensory traits, it is valued in flavor and fragrance applications. Chemically, it has the formula C12H22O2 and is known by several synonyms including (-)-menthyl acetate and L-acetic acid p-menth-3-yl ester.
Where does laevo-menthyl acetate occur naturally and how is it used?
Laevo-menthyl acetate naturally occurs in various plants, notably in peppermint, spearmint, eucalyptus oil, cornmint, lemon balm, raspberry, mango fruit, and buchu oil. Its natural presence contributes to the characteristic minty and fresh notes of these botanicals. Industrially, it is utilized as a flavor and fragrance ingredient to impart cooling and minty notes in consumer products such as oral care items, beverages, confectionery, and perfumes. Usage is carefully controlled based on guidelines established by bodies such as FEMA (US) and IFRA (Global) to ensure safety and efficacy in applications.
What are the regulatory standards and safety considerations for laevo-menthyl acetate?
Regulatory bodies recognize laevo-menthyl acetate as generally safe for use in flavors and fragrances when used within prescribed limits. It is listed as Generally Recognized As Safe (GRAS) by the FEMA (US) Expert Panel for flavor use, with specific maximum concentrations defined for various product categories. The compound is also subject to the IFRA Code of Practice guidelines for fragrance ingredients. Safety data indicate low toxicity, with oral and dermal LD50 values exceeding 5000 mg/kg in animal studies. It may act as an irritant to skin and respiratory systems at high concentrations, so precautionary measures such as protective gloves and eyewear are recommended during handling. Its stability across cosmetic formulations contributes to its safe incorporation into personal care products.

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

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
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C09870
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2915.39.9000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
Formulations/Preparations:
grade: 95% min. l-isomer

General Material Information

Preferred name laevo-menthyl acetate
Trivial Name (-)-Menthyl acetate
Short Description L-menthyl acetate
Formula C12 H22 O2
CAS Number 2623-23-6
ECHA Number 220-076-0
FDA UNII W8C5F4H1OA
Nikkaji Number J71.002D
COE Number 206
xLogP3-AA 3.60 (est)
Bio Activity Summary External link
NMR Predictor External link
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
Synonyms
  • L- acetic acid p-menth-3-yl ester
  • laevo- acetic acid para-menth-3-yl ester
  • L- acetic acid, p-menth-3-yl ester
  • L-p- menth-3-yl acetate
  • laevo-para- menth-3-yl acetate
  • menthol acetate
  • (-)- menthyl acetate
  • (1R,3R,4S)-(-)- menthyl acetate
  • (1R)-(-)- menthyl acetate
  • L- menthyl acetate
  • nat. menthyl acetate
  • laevo- menthyl acetate (natural)
  • menthyl acetate laevo
  • menthyl acetate natural
  • menthyl acetate-l
  • L- menthyle acetate
  • (1R-(1alpha,2beta,5alpha))-5-methyl-2-(1-methyl ethyl) acetate
  • (1R-(1alpha,2beta,5alpha))-5-methyl-2-(1-methylethyl) acetate
  • (5-methyl-2-propan-2-ylcyclohexyl) acetate
  • L-2-iso propyl-5-methyl cyclohexan-1-ol acetate
  • laevo-2-iso propyl-5-methyl cyclohexan-1-ol acetate
  • L-2-iso propyl-5-methylcyclohexan-1-ol acetate
  • [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] acetate
  • Cyclohexanol, 5-methyl-2-(1-methylethyl)-, 1-acetate, (1R,2S,5R)-
  • Menthol, acetate, (1R,3R,4S)-(-)-
  • Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate, [1R-(1α,2β,5α)]-
  • Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate, (1R,2S,5R)-
  • (-)-Menthyl acetate
  • L-Menthyl acetate
  • l-Menthol acetate
  • l-(-)-Menthyl acetate
  • (1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexanol acetate
  • (-)-Menthol acetate
  • NSC 3722
  • NSC 52970
  • (-)-p-Menthyl acetate
  • Acetic acid (R)-menthyl ester

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 198.30574035645
Specific gravity @ 20 °C
Pounds per Gallon 7.698 to 7.731
Refractive Index 1.445 to 1.448 @ 20 °C
Optical Rotation -70 to -75
Boiling Point 229 to 230°C @ 760 mm Hg
Acid Value 2 max KOH/g
Vapor Pressure 0.071 mmHg @ 25 °C
Flash Point TCC Value 87 °C TCC
logP (o/w) 4.182 est
Solubility
alcohol Yes
fixed oils Yes
propylene glycol Yes
water, slightly Yes
water, 17.13 mg/L @ 25 °C (est) Yes
Stability
bath foam Unspecified
cream Unspecified
hair spray Unspecified
lipstick Unspecified
lotion Unspecified
non-discoloring in most media Unspecified
soap Unspecified

Organoleptic Properties

Odor Type: Mentholic
mentholic, minty, herbal, tea, fruity, woody, floral, earthy
Odor strength medium
Substantivity 10 hour(s) at 100.00 %
Luebke, William tgsc, (2021) At 100.00 %. mentholic minty herbal tea fruity woody floral earthy
Flavor Type: Minty
cooling, mentholic, minty, herbal, woody old wood, balsamic, clove, tropical
Luebke, William tgsc, (2021) Cooling mentholic minty herbal old wood balsamic clove tropical floral
Useful in: mint, sweet others. Sweet minty, slightly fruity
Luebke, William tgsc, (2017) Cooling mentholic minty tropical balsamic floral woody
General comment FRESH

Occurrences

Potential Uses

Applications
Odor purposes Blueberry , Caraway seed , Citrus , Herbal , Lavender , Mint , Peach , Peppermint , Raspberry
Flavoring purposes Caraway seed
Other purposes Lifter
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)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Human Experience:
8 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
oral-rat LD50 > 5000 mg/kg
Food and Cosmetics Toxicology. Vol. 14, Pg. 477, 1976.

Dermal Toxicity:
skin-rabbit LD50 > 5000 mg/kg
Food and Cosmetics Toxicology. Vol. 14, Pg. 477, 1976.

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
Recommendation for laevo-menthyl acetate usage levels up to:
8.0000 % in the fragrance concentrate.
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 ppmaverage maximum ppm
baked goods: -24.00000
beverages(nonalcoholic): -5.50000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: -5.20000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -4.00000
fruit ices: -4.00000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: -26.00000
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

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):2623-23-6
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :220674
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 3082
WGK Germany:2
[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] acetate
Chemidplus:0002623236
RTECS:AI5900000 for cas# 2623-23-6