Terpineol is any of four isomericmonoterpenoids. 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.
Synthesis and biosynthesisedit
Although it is naturally occurring, terpineol is commonly manufactured from alpha-pinene, which is hydrated in the presence of sulfuric acid.[4]
The biosynthesis of α-terpineol proceeds from geranyl pyrophosphate, which releases pyrophosphate to give the terpinyl cation. This carbocation is the precursor to many terpenes and terpenoids. Its hydrolysis gives terpineol.
^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.
^Yuasa, Yoshifumi; Yuasa, Yoko (2006). "A Practical Synthesis of d-α-Terpineol via Markovnikov Addition of d-limonene Using Trifluoroacetic Acid". Organic Process Research & Development. 10 (6): 1231–1232. doi:10.1021/op068012d.
^Davis, Edward M.; Croteau, Rodney (2000). "Cyclization enzymes in the biosynthesis of monoterpenes, sesquiterpenes, and diterpenes". Biosynthesis. Vol. 209. pp. 53–95. doi:10.1007/3-540-48146-X_2. ISBN978-3-540-66573-1. {{cite book}}: |journal= ignored (help)
External linksedit
MSDS for alpha-terpineol
Media related to Terpineols at Wikimedia Commons
January 01, 1970
terpineol, four, isomeric, monoterpenoids, terpenoids, terpene, that, modified, addition, functional, group, this, case, alcohol, have, been, isolated, from, variety, sources, such, cardamom, cajuput, pine, petitgrain, four, isomers, exist, terpineol, terpinen. 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 a b g terpineol and terpinen 4 ol b and g terpineol differ only by the location of the double bond Terpineol is usually a mixture of these isomers with a terpineol as the major constituent alpha terpineol Skeletal formula Ball and stick model Names IUPAC names p Menth 1 en 8 ol2 4 Methylcyclohex 3 en 1 yl propan 2 ol Other names 2 4 Methyl 1 cyclohex 3 enyl propan 2 olalpha terpineola terpineola a 4 Trimethylcyclohex 3 ene 1 methanolTerpene alcohol Identifiers CAS Number a 98 55 5 Yb 138 87 4g 586 81 24 562 74 3 3D model JSmol a Interactive image Beilstein Reference 2325137 ChEBI a CHEBI 22469 Yb CHEBI 132899g CHEBI 811514 CHEBI 78884 ChEMBL a ChEMBL507795 N4 ChEMBL507795 ChemSpider a 13850142 Yb 8418g 109834 10756 EC Number a 202 680 6b 205 342 6g 209 584 34 209 235 5 KEGG b C175174 C17073 PubChem CID a 17100b 8748g 114674 11230 UNII a 21334LVV8W Yg 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 YKey WUOACPNHFRMFPN UHFFFAOYSA N Ya InChI 1 C10H18O c1 8 4 6 9 7 5 8 10 2 3 11 h4 9 11H 5 7H2 1 3H3Key WUOACPNHFRMFPN UHFFFAOYAL SMILES a C C1 C CC CC1 C O C C Properties Chemical formula C 10H 18O 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 x 111 9 10 6 cm3 mol Hazards NFPA 704 fire diamond 210 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 Y N Infobox references 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 a Terpineol is one of the two most abundant aroma constituents of lapsang souchong tea the a terpineol originates in the pine smoke used to dry the tea 3 a terpineol is a chemical constituent of skullcap Synthesis and biosynthesis editAlthough it is naturally occurring terpineol is commonly manufactured from alpha pinene which is hydrated in the presence of sulfuric acid 4 An alternative route starts from limonene 5 nbsp Terpineol synthesis from limonene Limonene reacts with trifluoroacetic acid in a Markovnikov addition to a trifluoroacetate intermediate which is easily hydrolyzed with sodium hydroxide to a terpineol with 7 selectivity Side products are b terpineol in a mixture of the cis isomer the trans isomer and 4 terpineol The biosynthesis of a terpineol proceeds from geranyl pyrophosphate which releases pyrophosphate to give the terpinyl cation This carbocation is the precursor to many terpenes and terpenoids Its hydrolysis gives terpineol nbsp Biosynthetic conversion of geranyl pyrophosphate to the terpenes a pinene and b pinene right and to a terpineol bottom left 6 References edit a b c d e f Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health Merck Index 11th Edition 9103 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 Gscheidmeier Manfred Fleig Helmut Turpentines 16 Pine Oil Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a27 267 ISBN 978 3527306732 Yuasa Yoshifumi Yuasa Yoko 2006 A Practical Synthesis of d a Terpineol via Markovnikov Addition of d limonene Using Trifluoroacetic Acid Organic Process Research amp Development 10 6 1231 1232 doi 10 1021 op068012d Davis Edward M Croteau Rodney 2000 Cyclization enzymes in the biosynthesis of monoterpenes sesquiterpenes and diterpenes Biosynthesis Vol 209 pp 53 95 doi 10 1007 3 540 48146 X 2 ISBN 978 3 540 66573 1 a href Template Cite book html title Template Cite book cite book a journal ignored help External links editMSDS for alpha terpineol nbsp Media related to Terpineols at Wikimedia Commons Retrieved from https en wikipedia org w index php title Terpineol amp oldid 1152471795, wikipedia, wiki, book, books, library,
