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Terpineol information


alpha-terpineol
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
IUPAC names
p-Menth-1-en-8-ol
2-(4-Methylcyclohex-3-en-1-yl)propan-2-ol
Other names
2-(4-Methyl-1-cyclohex-3-enyl)propan-2-ol
alpha-terpineol
α-terpineol
α,α,4-Trimethylcyclohex-3-ene-1-methanol
Terpene alcohol
Identifiers
CAS Number
  • α: 98-55-5 checkY
  • β: 138-87-4
  • γ: 586-81-2
  • 4-: 562-74-3
3D model (JSmol)
  • α: Interactive image
Beilstein Reference
2325137
ChEBI
  • α: CHEBI:22469 checkY
  • β: CHEBI:132899
  • γ: CHEBI:81151
  • 4-: CHEBI:78884
ChEMBL
  • α: ChEMBL507795 ☒N
  • 4-: ChEMBL507795
ChemSpider
  • α: 13850142 checkY
  • β: 8418
  • γ: 10983
  • 4-: 10756
EC Number
  • α: 202-680-6
  • β: 205-342-6
  • γ: 209-584-3
  • 4-: 209-235-5
KEGG
  • β: C17517
  • 4-: C17073
PubChem CID
  • α: 17100
  • β: 8748
  • γ: 11467
  • 4-: 11230
UNII
  • α: 21334LVV8W checkY
  • γ: 5PH9U7XEWS
CompTox Dashboard (EPA)
  • 4-: DTXSID4044824
InChI
  • InChI=1S/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3 checkY
    Key: WUOACPNHFRMFPN-UHFFFAOYSA-N checkY
  • α: InChI=1/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3
    Key: WUOACPNHFRMFPN-UHFFFAOYAL
SMILES
  • α: C\C1=C\CC(CC1)C(O)(C)C
Properties
Chemical formula
C10H18O
Molar mass 154.253 g·mol−1
Appearance Colorless liquid[1]
Density 0.93 g/cm3[1]
Melting point −35.9 to −28.2 °C (−32.6 to −18.8 °F; 237.2 to 245.0 K)[1] (mixture of isomers)
Boiling point 214–217 °C (417–423 °F; 487–490 K)[1] (mixture of isomers)
Solubility in water
2.42 g/L[1]
Magnetic susceptibility (χ)
−111.9·10−6 cm3/mol
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point 88 °C (190 °F; 361 K)[1]
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Terpineol is any of four isomeric monoterpenoids. Terpenoids are terpene that are modified by the addition of a functional group, in this case, an alcohol. Terpineols have been isolated from a variety of sources such as cardamom, cajuput oil, pine oil, and petitgrain oil.[2] Four isomers exist: α-, β-, γ-terpineol, and terpinen-4-ol. β- and γ-terpineol differ only by the location of the double bond. Terpineol is usually a mixture of these isomers with α-terpineol as the major constituent.

Terpineols: alpha-, beta-, gamma-, and the 4-terpineol isomer

Terpineol has a pleasant odor similar to lilac and is a common ingredient in perfumes, cosmetics, and flavors. α-Terpineol is one of the two most abundant aroma constituents of lapsang souchong tea; the α-terpineol originates in the pine smoke used to dry the tea.[3] (+)-α-terpineol is a chemical constituent of skullcap.

  1. ^ a b c d e f Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ^ Merck Index, 11th Edition, 9103
  3. ^ Shan-Shan Yao; Wen-Fei Guo; Yi Lu; Yuan-Xun Jiang (2005). "Flavor Characteristics of Lapsang Souchong and Smoked Lapsang Souchong, a Special Chinese Black Tea with Pine Smoking Process". Journal of Agricultural and Food Chemistry. 53 (22): 8688–93. doi:10.1021/jf058059i. PMID 16248572.

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Terpineol

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Terpineol is any of four isomeric monoterpenoids. Terpenoids are terpene that are modified by the addition of a functional group, in this case, an alcohol...

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Tea tree oil

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found four of the constituent chemicals (eucalyptol, 4-terpineol, dipentene, and alpha-terpineol) are endocrine disruptors, raising concerns of potential...

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Sichuan pepper

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(India) — Sabinene, limonene, pinenes, para-cymene, terpinenes, 4-terpineol, alpha-terpineol. (Zeitschrift f. Lebensmitteluntersuchung und -forschung A, 206...

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Limonene

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addition of trifluoroacetic acid followed by hydrolysis of the acetate gives terpineol. The most widely practiced conversion of limonene is to carvone. The three-step...

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Bay leaf

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methyleugenol, and other α- and β-pinenes, phellandrene, linalool, geraniol, terpineol, and also contain lauric acid.[citation needed] If eaten whole, Laurus...

Word Count : 1834

Thyme

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leaves is thymol 8.55 mg/g. Other components are carvacrol, linalool, α-terpineol, and 1,8-cineole. Several are also found in basil. Some exhibit antioxidant...

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Oregano

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γ-terpinene, caryophyllene, spathulenol, germacrene D, β-fenchyl alcohol and δ-terpineol. Drying of the plant material affects both quantity and distribution of...

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Cardamom

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storage conditions and may be as high as 8%. The oil is typically 45% α-terpineol, 27% myrcene, 8% limonene, 6% menthone, 3% β-phellandrene, 2% 1,8-cineol...

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Bursera graveolens

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rheumatism. Aged heartwood is rich in terpenes such as limonene and α-terpineol. In 2006, the government of Peru listed Bursera graveolens as "In Critical...

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Kewra

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(65.6–75.4%), Terpinen-4-ol (11.7–19.5%), p-Cymene (1.0–3.1%) and Alpha Terpineol (1.2–2.9%) Ganjam Kewda Flower Ganjam Kewda Rooh Adkar PP, Bhaskar VH...

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Strawberry

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2-heptanol 2-heptanone 2-methyl butanoic acid 2-methylbutyl acetate alpha-terpineol amyl acetate amyl butyrate benzaldehyde benzyl acetate butyl acetate butyl...

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Nutmeg

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terpenes and phenylpropanoids, including D-pinene, limonene, D-borneol, L-terpineol, geraniol, safrol, and myristicin. In its pure form, myristicin is a toxin...

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Ethanol

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alcohols Borneol Citronellol Geraniol Linalool Menthol Nerol Rhodinol Terpineol Sesquiterpene alcohols Bisabolol Farnesol Nerolidol Patchoulol Diterpene...

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Lavandula stoechas

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contain ketones (d-camphor and d-fenchone) and alcohols (borneol and terpineol). Since its introduction into Australia, it has become an invasive species...

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Geraniol

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CBGA. In acidic solutions, geraniol is converted to the cyclic terpene α-terpineol. The alcohol group undergoes expected reactions. It can be converted to...

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Pine oil

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turpentine. Both synthetic and natural pine oil consists mainly of α-terpineol, a C10 alcohol (b.p. 214–217 °C). The detailed composition of natural...

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Terpenoid

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terpenoids. Selected terpenoids Paclitaxel is a diterpenoid anticancer drug. Terpineols are monoterpenoids. Humulones are classified as sesquiterpenoids. Retinol...

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Turpentine

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fragrant chemical compounds. Commercially used camphor, linalool, alpha-terpineol, and geraniol are all usually produced from alpha-pinene and beta-pinene...

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Cedrus deodara

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dihydroflavonol). The main components of the needle essential oil include α-terpineol (30.2%), linalool (24.47%), limonene (17.01%), anethole (14.57%), caryophyllene...

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Lavender oil

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latifolia Terpenes / Monoterpenols Linalool 28.92 % 49.47 % α-Terpineol 0.90% 1.08% γ-Terpineol 0.09% Borneol 1.43% Isoborneol 0.82% Terpinen-4-ol 4.32% Nerol...

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C10H18O

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Lavandulol Linalool Menthone Myrcenol Nerol 2-Pinanol Rose oxide Terpinen-4-ol Terpineol This set index page lists chemical structure articles associated with...

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Jeyes Fluid

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T;R24/25. Xi;R38 Propan-2-ol (isopropyl alcohol) 200-661-7 67-63-0 1–2.5% F;R11 Xi;R36 R67 Terpineol (for fragrance) 232-268-1 8000-41-7 2.5–5% Xi;R38...

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Cycloalkane

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gives less information about the compound. An example of a common name is terpineol, the name of which can tell us only that it is an alcohol (because the...

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Chamaecyparis obtusa

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limonene, terpinen-4-ol, eudesmols, α-terpinyl acetate, α-terpinolene, α-terpineol, 3-carene, α-pinene, γ-terpinene, camphene, bornyl acetate, 1-methyladamantane...

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Coleus amboinicus

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γ-terpinene (7.76%), p-cymene (6.46%), caryophyllene oxide (5.85%), α-terpineol (3.28%), and β-selinene (2.01%). Another analysis obtained thymol (41...

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Terpene

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C10H16. Examples of monoterpenes and monoterpenoids include geraniol, terpineol (present in lilacs), limonene (present in citrus fruits), myrcene (present...

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