Terpineol

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 470602595

| Name = alpha-terpineol

| ImageFileL1 = Terpineol alpha.svg

| ImageNameL1 = Skeletal formula

| ImageFileR1 = Alpha-terpineol-3D-balls.png

| ImageNameR1 = Ball-and-stick model

| ImageName = alpha-Terpineol

| IUPACNames = p-Menth-1-en-8-ol
2-(4-Methylcyclohex-3-en-1-yl)propan-2-ol

| OtherNames = 2-(4-Methyl-1-cyclohex-3-enyl)propan-2-ol
alpha-terpineol
α-terpineol
α,α,4-Trimethylcyclohex-3-ene-1-methanol
Terpene alcohol

| Section1 = {{Chembox Identifiers

| index_label = α

| index1_label = β

| index2_label = γ

| index3_label = 4-

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 98-55-5

| CASNo1 = 138-87-4

| CASNo2 = 586-81-2

| CASNo3 = 562-74-3

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 22469

| ChEBI1 = 132899

| ChEBI2 = 81151

| ChEBI3 = 78884

| Beilstein = 2325137

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 13850142

| ChemSpiderID1 = 8418

| ChemSpiderID2 = 10983

| ChemSpiderID3 = 10756

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 507795

| ChEMBL3 = 507795

| DTXSID3 = DTXSID4044824

| EC_number = 202-680-6

| EC_number1 =205-342-6

| EC_number2 = 209-584-3

| EC_number3 = 209-235-5

| KEGG1 = C17517

| KEGG3 = C17073

| PubChem = 17100

| PubChem1 = 8748

| PubChem2 = 11467

| PubChem3 = 11230

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 21334LVV8W

| UNII2 = 5PH9U7XEWS

| InChI = 1/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3

| InChIKey = WUOACPNHFRMFPN-UHFFFAOYAL

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = WUOACPNHFRMFPN-UHFFFAOYSA-N

| SMILES = C\C1=C\CC(CC1)C(O)(C)C

}}

| Section2 = {{Chembox Properties

| C=10 | H=18 | O=1

| Density = 0.93{{nbsp}}g/cm³

| MeltingPtC = -35.9 to -28.2

| MeltingPt_notes = (mixture of isomers)

| MeltingPt_ref = {{GESTIS|ZVG=122876}}

| BoilingPtC = 214–217

| BoilingPt_notes = (mixture of isomers)

| BoilingPt_ref =

| Solubility = 2.42{{nbsp}}g/L

| Appearance = Colorless liquid

|Odor = Pleasant, lilac-like

| MagSus = −111.9·10⁻⁶{{nbsp}}cm³/mol

}}

| Section3 = {{Chembox Hazards

| ExternalSDS = [http://hazard.com/msds/mf/baker/baker/files/t0364.htm External MSDS]

| NFPA-H = 2

| NFPA-F = 1

| NFPA-R = 0

| NFPA-S =

| HPhrases =

| PPhrases =

| GHS_ref =

| FlashPtC = 88

| FlashPt_ref =

}}

}}

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.{{Merck11th|page=9103}} Four isomers exist: α-terpineol, β-terpineol, γ-terpineol, and terpinen-4-ol. β-Terpineol 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.

:Image:Terpineols.png{{clear left}}

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.{{cite journal|first1=Shan-Shan |last1=Yao |first2=Wen-Fei |last2=Guo |first3=Yi |last3=Lu |first4=Yuan-Xun |last4=Jiang |year=2005 |title=Flavor Characteristics of Lapsang Souchong and Smoked Lapsang Souchong, a Special Chinese Black Tea with Pine Smoking Process |journal=Journal of Agricultural and Food Chemistry |volume=53 |issue=22 |url=http://d.wanfangdata.com.cn/NSTLQK_NSTL_QK10615205.aspx | doi = 10.1021/jf058059i |pmid=16248572 |pages=8688–93|bibcode=2005JAFC...53.8688Y |url-access=subscription }} (+)-α-Terpineol is a chemical constituent of skullcap.