(-)-alpha-terpineol

(-)-alpha-terpineol is a monoterpene alcohol with a lilac floral terpenic odor, used primarily as a flavor and fragrance agent in various cosmetic and food applications.

General Material Description

(-)-alpha-terpineol is a naturally derived monoterpene alcohol characterized by the molecular formula C₁₀H₁₈O. It typically appears as a colorless to pale yellow liquid with a distinct lilac floral terpenic odor profile. This compound has numerous synonyms including (S)-(-)-p-menth-1-en-8-ol and L-alpha-terpineol, reflecting its stereochemistry and source identification. (-)-alpha-terpineol is commonly found in essential oils such as bay laurel leaf oil and Melaleuca alternifolia (tea tree) oil. Its derivatives and enantiomers contribute similarly to aroma and flavor formulations. For detailed chemical information and nomenclature, consult the PubChem database. The compound is generally extracted from plant sources or synthesized for use in both flavor and fragrance industries.

Occurrence, Applicability & Potential Uses

(-)-alpha-terpineol occurs naturally in various plant-derived essential oils, including bay laurel leaf oil, species of Cinnamomum, mint, and notably in Australian tea tree oil (Melaleuca alternifolia) at approximately 0.69%. It is widely utilized as a flavor and fragrance agent, imparting lilac floral, terpenic, and fresh herbal notes. Its application extends to perfuming agents in cosmetics and flavoring substances in foods and beverages. The compound is subject to safety and usage regulations such as FEMA (US), which recognizes it as generally safe for flavoring up to defined concentration thresholds, and IFRA (Global), which sets guidelines on usage levels in fine fragrances to ensure consumer safety.

Physico-Chemical Properties Summary

(-)-alpha-terpineol exhibits physical properties conducive to its use in flavor and fragrance formulations. It is a volatile monoterpene alcohol with a boiling point ranging from 217 to 218 °C at atmospheric pressure and a melting point between 31 and 35 °C. This compound has a moderate logP value of 3.28, indicating lipophilicity suitable for incorporation in various matrices. The specific gravity measured at 15 °C ranges from 0.935 to 0.943, and its refractive index at 20 °C varies between 1.479 and 1.486. It has low vapor pressure (0.028 mmHg at 25 °C), impacting volatility and evaporation rates. Solubility is confirmed in alcohol and to a limited extent in water (~371.7 mg/L at 25 °C), which influences formulation compatibility. The shelf life is typically at least 24 months when stored in cool, dry conditions protected from heat and light. These properties determine its behavior in product development and application.

FAQ

What is (-)-alpha-terpineol and what are its main characteristics?

(-)-alpha-terpineol is a monoterpene alcohol naturally present in essential oils such as bay laurel and tea tree oil. It is noted for its characteristic lilac floral and terpenic odor. The compound has the molecular formula C₁₀H₁₈O and appears as a colorless to pale yellow liquid. It has several chemical synonyms reflecting its stereochemistry. This compound serves as a key ingredient in flavor and fragrance formulations due to its aromatic profile.

Where does (-)-alpha-terpineol occur and what are its primary applications?

This compound naturally occurs in numerous plant sources including bay laurel leaf oil, mint, various Cinnamomum species, and Melaleuca alternifolia (tea tree oil). It is primarily applied in the flavor and fragrance industries, enhancing products with floral and fresh terpene-like notes. It is commonly incorporated in cosmetic perfuming agents, as well as in food and beverage flavorings, where it replicates or enhances herbal, floral, and fruity nuances.

What regulations and safety guidelines apply to (-)-alpha-terpineol?

(-)-alpha-terpineol is regulated under standards such as FEMA (US) and IFRA (Global) which establish safe use levels in food flavorings and cosmetic fragrances. IFRA provides specific limits for skin contact, recommending usage levels up to 0.77% in fine fragrances and 0.18% in cosmetic formulations to ensure user safety. The compound is classified as an irritant under European regulations, requiring caution in handling to avoid skin or eye contact. Safety data sheets and assessments by RIFM and FEMA support its controlled and responsible use.

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
Metabolomics Database:	Search
KEGG (GenomeNet):	C11393
HMDB (The Human Metabolome Database):	HMDB36086
FooDB:	FDB014922
Export Tariff Code:	2906.14.0000
Typical G.C.
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View
Wikipedia:	View

General Material Information

Preferred name	(-)-alpha-terpineol
Trivial Name	(-)-α-Terpineol
Short Description	L-alpha-terpineol
Formula	C10 H18 O
CAS Number	10482-56-1
ECHA Number	233-986-8
FDA UNII	21M14KDA67
Nikkaji Number	J9.809D
Beilstein Number	2325137
MDL	MFCD00075926
xLogP3-AA	1.80 (est)
NMR Predictor	External link
Synonyms	3-cyclohexene-1-methanol, a,a,4-trimethyl-, (1S)- 3-cyclohexene-1-methanol, a,a,4-trimethyl-, (S)- (4S)-p- menth-1-en-8-ol (S)-(-)-p- menth-1-en-8-ol (S)-(-)-para- menth-1-en-8-ol p- menth-1-en-8-ol, (S)-(-)- (4S)-p- menth-1-en-8-ol; 2-[(1S)-4-methylcyclohex-3-en-1-yl]propan-2-ol 2-[(1S)-4-methyl-1-cyclohex-3-enyl]propan-2-ol 2-[(1S)-4-methyl-3-cyclohexen-1-yl]-2-propanol (S)-2-(4-methyl-3-cyclohexenyl)-2-propanol 2-[(1S)-4-methylcyclohex-3-en-1-yl]propan-2-ol (-)-a- terpineol (L)-a- terpineol (S)-(-)-a- terpineol (S)-a- terpineol L-a- terpineol L-alpha- terpineol laevo-alpha- terpineol (1S)-a,a,4-trimethyl-3-cyclohexene-1-methanol (S)-a,a,4-trimethyl-3-cyclohexene-1-methanol (S)-alpha,alpha,4-trimethyl-3-cyclohexene-1-methanol 2-[(1S)-4-methyl-1-cyclohex-3-enyl]propan-2-ol 3-Cyclohexene-1-methanol, α,α,4-trimethyl-, (1S)- p-Menth-1-en-8-ol, (S)-(-)- 3-Cyclohexene-1-methanol, α,α,4-trimethyl-, (S)- (1S)-α,α,4-Trimethyl-3-cyclohexene-1-methanol l-α-Terpineol (-)-α-Terpineol α-Terpineol, (-)- (S)-α-Terpineol (S)-(-)-α-Terpineol (S)-(-)-Terpineol (S)-α,α,4-Trimethyl-3-cyclohexene-1-methanol 2-[(1S)-4-Methylcyclohex-3-en-1-yl]propan-2-ol L-Alpha-terpineol

Suppliers

Augustus Oils	BOC Sciences
Lluch Essence	Moellhausen
Parchem	Penta International
Seqens	Sigma-Aldrich
SRS Aromatics	Augustus Oils Ltd
Penta International Corporation	SRS Aromatics Ltd

PhysChem Properties

Material listed in food chemical codex	Yes
Molecular weight	154.2526550293
Specific gravity	@ 15 °C
Pounds per Gallon	7.796 to 7.863
Refractive Index	1.479 to 1.486 @ 20 °C
Melting Point	31 to 35°C @ 760 mm Hg
Boiling Point	217 to 218°C @ 760 mm Hg
Vapor Pressure	0.028 mmHg @ 25 °C
Flash Point TCC Value	90 °C TCC
logP (o/w)	3.28
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
water, 371.7 mg/L @ 25 °C (est)	Yes
water	No

Organoleptic Properties

Odor Type: Terpenic
lilac, floral, terpenic
General comment	At 100.00 %. lilac floral terpenic

Occurrences

Potential Uses

Applications	flavor and fragrance agents
Odor purposes	Acacia , Aldehydic , Almond , Amber , Anise , Apple blossom , Apricot , Balsam , Bay rum , Bayberry , Bergamot , Bluebell , Bois de rose , Bouquet , Bubble gum , Cajeput , Cardamom oil replacer , Carnation , Cassia , Cedarwood , Cherry , Christmas , Cinnamon , Citrus , Clary sage oil replacer , Clover , Country meadow , Crabapple blossom , Cubeb , Cypress oil replacer , Dillenia , Elder flower , Eucalyptus oil replacer , Evergreen , Fagonia , Fern , Fig , Fir needle oil replacer , Floral , Frangipani plumeria , Fresh outdoors , Gardenia , Genet , Geranium , Grape , Grapefruit , Green , Green grass , Greenhouse , Hawthorn , Herbal , Hollyberry , Honeysuckle , Hyacinth , Jasmin , Jonesia , Juniper , Juniper berry , Lavandin , Lavender , Leather , Lemon , Lemongrass , Licorice , Lilac , Lily , Lily of the valley , Lime , Linaloe wood , Linden flower , Lotus , Lovage root , Lychee , Mace , Magnolia , Mango , Mimosa , Mulberry , Musk , Narcissus , Neroli , Niaouli , Nutmeg , Orange , Orange blossom , Passion fruit , Peach , Pennyroyal , Peony , Petitgrain , Pine forest , Pineapple , Plum mirabelle plum , Potpourri , Powder , Rain , Raspberry , Rose , Sandalwood , Sassafras , Snake root , Spearmint , Spice , Sweet pea , Tea green tea , Thyme oil white replacer , Tuberose , Valerian , Valerian , Wallflower , Wintergreen , Wisteria , Woody
Flavoring purposes	Cajeput , Cubeb , Linaloe wood , Lovage root , Pennyroyal , Snake root , Valerian , Valerian
Other purposes	Strawberry leaf
Cosmetic purposes	Perfuming agents

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/38 - Irritating to skin and 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 36 - Wear suitable protective clothing.

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:
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
maximum skin levels for fine fragrances:
	0.7700 % 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 (-)-alpha-terpineol usage levels up to:
	30.0000 % in the fragrance concentrate.
use level in formulae for use in cosmetics:
	0.1800 %
Dermal Systemic Exposure in Cosmetic Products:
	0.0046 mg/kg/day (IFRA, 2004)

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:		-	19.00000
beverages(nonalcoholic):		-	5.40000
beverages(alcoholic):		-	-
breakfast cereal:		-	-
cheese:		-	-
chewing gum:		-	40.00000
condiments / relishes:		-	38.00000
confectionery froastings:		-	-
egg products:		-	-
fats / oils:		-	-
fish products:		-	-
frozen dairy:		-	16.00000
fruit ices:		-	16.00000
gelatins / puddings:		12.00000	16.00000
granulated sugar:		-	-
gravies:		-	-
hard candy:		-	14.00000
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:		-	-