Molecular & Flavor Profile
Common name:	alpha-TERPINEOL
IUPAC name:	2-(4-methylcyclohex-3-en-1-yl)propan-2-ol
SMILES:	CC1=CCC(CC1)C(C)(C)O
CAS:	8000-41-7, 10482-56-1, 2438-12-2, 98-55-5
Flavor Profile:	Not Available
FEMA Flavor Profile:	Anise , Fresh , Mint , Oil
FEMA Number:	3045
Taste:	lime (distilled) peach, floral (lilac) flavor sweet, lime taste
Odor:	floral, lilac
Functional Groups:	hydroxy compound, alcohol, tertiary alcohol, alkene

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External IDs

PubChem ID:	17100
FooDB ID:	NA
SuperSweet ID:	NA
BitterDB ID:	NA

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Entities that contain alpha-TERPINEOL

Physicochemical Properties

Molecular weight: 154.253 g/mol
HBD count: 1
HBA count: 1
Number of rotatable bonds: 1
Complexity: 168.0
Topological Polor Surface Area: 20.2 A^2
Monoisotopic Mass: 154.136 g/mol
Exact Mass: 154.136 g/mol
XlogP: 1.8
Charge: 0 C(coulomb)
Heavy Atom Count: 11
Atom Stereocenter Count: 1
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 1
Bond Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently Bonded Unit Count: 1
InChI: InChI=1S/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3
Volume 3D: 132.2

Nomenclature

Common name: alpha-TERPINEOL
IUPAC name: 2-(4-methylcyclohex-3-en-1-yl)propan-2-ol
CAS numbers: 8000-41-7, 10482-56-1, 2438-12-2, 98-55-5
SMILES: CC1=CCC(CC1)C(C)(C)O
InChI: InChI=1S/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3
FlavorDB/FEMA name: alpha,alpha-4-Trimethyl-3-cyclohexene-1-methanol
FL number: 2.014
NAS number: 3045
CoE number: 62
EINECS number: 202-680-6
JECFA number: 366

Description

FEMA flavor profile: Anise, Fresh, Mint, Oil
Odor: floral, lilac
Taste: lime (distilled)
peach, floral (lilac) flavor
sweet, lime taste
Functional groups: hydroxy compound, alcohol, tertiary alcohol, alkene
Bitter compound: No
Source description: α-Terpineol has a characteristic lilac odor with a sweet taste reminiscent of peach on dilution

Regulatory Status

CoE status: 40 ppm
FDA status: 21 CFR 172.515; 27 CFR 21 et seq
FDA notes: Approved as an excipient (CDER, 1996)
JECFA status: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (1998)

Aroma/Taste Threshold Values

Aroma threshold values: pine-like, woody and resinous with a slight cooling lemon and lime citrus nuance, and a floral dry out
Taste threshold values: Taste characteristics at 2 to 25 ppm; woody, terpy, lemon and lemon–lime-like with a slight herbal and floral nuance. Taste characteristics at 10 to 25 ppm:citrus woody with a lemon and lime nuance. It has a slight soapy mouthfeel

Natural Occurence

Occurrence summary: Naturally occurring; Reported in 118 FlavorDB source entities
Source entity count: 118
Representative sources: Wort, Beer, Cognac Brandy, Rum, Wine, Bilberry Wine, Botrytized Wine, Champagne, Plum Wine, Port Wine
Documented natural occurrence: Reported found in more than 150 derivatives from leaves, herbs and flowers; the d-, l- and dl-isomers are known:the d-form is found in the essential oils from Cupressaceae in general; also in the oils of Elettaria cardamomum, star anise, marjoram, clary sage, neroli and others. The l-form is found in Satureia montana, lavandin, cajeput, lime, lemon, cinnamon leaves and the distillates from Pinaceae (with exception of Pinus silvestris, which contains d-terpineol together with racemic form); like-wise, Nectandra elaiophora (wood) and petitgrain bigarade. The racemic form is found in cajenne linalool, Thymus caespititius, cajeput, Eucalyptus globulus; mixed with the l-form it is found in petitgrain; a nondefined form of terpineol has been reported in the bitter orange. Reported found in over 260 natural sources including apple, apple juice, apricot, sweet and sour cherry, citrus peel oils and juices, orange, lemon, lime, grapefruit, tangerine, mandarin peels oils and juices, bergamot, cranberry, blueberry, black currant, raspberry, strawberry, guava, grapes, raisin, melon, papaya, peach, pear, pineapple, carrot, celery, peas, potato, bell pepper, tomato, anise, cinnamon, clove, cumin seed, ginger, Mentha oils, pepper, mace, parsley, nutmeg, thyme, Gruyere cheese, parmesan cheese, butter, cooked chicken and beef, hop oil, beer, cognac, rum, wines, tea, nuts, honey, avocado, passion fruit, prune, plums, beans, mushroom, sweet and wild marjoram, starfruit, mango, tamarind, parsnip root, cardamom, coriander seed, rice, quince, litchi, cala-mus, dill, licorice, lovage root, juniper berry, corn oil, laurel, sweet and bitter fennel, wort, elderberry, loquat, myrtle berry, rosemary, buchu oil, Bourbon vanilla, mountain papaya, turmeric, clary sage, lemon balm, nectarines, naranjilla fruit, cape gooseberry and sea buckthorn

Composition

Molecular formula: C10H18O
Molecular composition: C: 0.779, H: 0.118, O: 0.104
Number of atoms: 11

ADMET Properties

ADMET Solubility: -2.384
ADMET Solubility Level: 3.0
ADMET BBB: 0.263
ADMET BBB Level: 1.0
ADMET EXT Hepatotoxic: -6.29785
ADMET EXT Hepatotoxic prediction md: False
ADMET EXT Hepatotoxic applicability: All properties and OPS components are within expected ranges.
ADMET EXT Hepatotoxic applicability md: 9.986289999999999
ADMET EXT Hepatotoxic applicability mdpvalue: 0.0927239
ADMET Absorption Level: 0.0
ADMET EXT PPB: -0.772684
ADMET EXT PPB prediction: True
ADMET EXT PPB applicability: All properties and OPS components are within expected ranges.
ADMET EXT PPB applicability md: 8.69161
ADMET EXT PPB applicability mdpvalue: 0.999243
ADMET unknown AlogP98: 0.0
ADMET AlogP98: 2.415
ADMET PSA 2D: 20.815

2D/3D Properties

Number of atoms: 11
Molecular formula: C10H18O
Molecular composition: C: 0.779, H: 0.118, O: 0.104
Molecular mass: 154.136 g/mol
Energy: 0.85 Kcal/M
AlogP: 2.415
LogD: 2.415
Molecular Solubilty: -2.3
Number of aromatic bonds: 0
Number of aromatic rings: 0
Number of H acceptor: 1
Number of H acceptor lipinski: 1
Number of H donor: 1
Number of H donor lipinski: 1
Number of H bonds: 0
Number of rings: 1
Surface area(SA): 196.58 A^2
Molecular SASA(Solvent accessible SA): 341.755 A^2
Radius of gyration: 1.67125 A
Molecular 3D SASA: 320.348 A^2

Consumption

Consumption: 20333.33 lb
Individual intake: 0.01723 mg/kg/day
Trade association guidelines: 3.723 mg
IOFI: Nature Identical

Specifications

Specifications: (JECFA, 2008); Appearance; Colorless, viscous liquid; Refractive index; 1.482–1.485 (20°C); Assay (min); 96% C10H18O; Solubility; 1 mL in 2 mL 70% alcohol, 4 mL 60% ; alcohol; slightly soluble in glycerol ; and water; Boiling point; 217°C; Specific gravity; 0.930–0.936 (25°C); Optical rotation; –35° to –15°

Reported Uses

Reported uses (ppm): (FEMA, 1994)

Food category usual/max:

Food category	Usual (ppm)	Max (ppm)
Alcoholic beverages	.58	2.12
Gravies	3.00	6.00
Baked goods	15.93	19.52
Hard candy	10.67	17.39
Chewing gum	13.53	83.47
Meat products	5.27	10.54
Condiments, relishes	25.91	44.55
Nonalcoholic beverages	3.40	5.41
Frozen dairy	9.23	14.00
Soft candy	13.51	16.50
Gelatins, puddings	8.56	12.64

Synthesis

Synthesis: Obtained from terpin hydrate by splitting off water; from pentane tricarboxylic acid by cyclization, followed by esterifi-cation to the hydroxy ester, then the unsaturated ester and Grignard to terpineol; also from isoprene and methyl vinyl ketone, using methyl magnesium iodide

Physical-Chemical Characteristics

Empirical formula / MW: C10H18O/154.25

Details of "Molecular & Flavor Profile" and physicochemical properties were obtained from PubChem Substance & Compound Databases, FooDB, Flavornet, SuperSweet, and BitterDB. 2D/3D and ADMET properties were obtained with Discovery Studio.