Chavicol

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 460027661

| Name = Chavicol

| ImageFile = Chavicol acsv.svg

| ImageAlt = Skeletal formula of chavicol

| ImageFile1 = Chavicol-3D-balls.png

| ImageAlt1 = Ball-and-stick model of the chavicol molecule

| PIN = 4-(Prop-2-en-1-yl)phenol

| OtherNames = 4-Allylphenol; p-Allylphenol; para-Allylphenol

|Section1={{Chembox Identifiers

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 108862

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

| ChEBI = 50158

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

| ChemSpiderID = 21105856

| SMILES = C=CCC1=CC=C(C=C1)O

| InChI = 1/C9H10O/c1-2-3-8-4-6-9(10)7-5-8/h2,4-7,10H,1,3H2

| InChIKey = RGIBXDHONMXTLI-UHFFFAOYAI

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

| StdInChI = 1S/C9H10O/c1-2-3-8-4-6-9(10)7-5-8/h2,4-7,10H,1,3H2

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

| StdInChIKey = RGIBXDHONMXTLI-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|changed|??}}

| CASNo = 501-92-8

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

| UNII = Q5ER4K6969

| PubChem = 68148

| EC_number = 207-929-2

| KEGG = C16930

}}

|Section2={{Chembox Properties

| Formula = C9H10O

| MolarMass = 134.18 g/mol

| Density = 1.020 g/cm3

| MeltingPtC = 16

| BoilingPtC = 238

| Solubility = 2.46 g/L

| BoilingPt_notes = (123 °C at 16 mmHg)

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Chavicol (p-allylphenol) is a natural phenylpropene, a type of organic compound.{{RubberBible86th}} Its chemical structure consists of a benzene ring substituted with a hydroxy group and a propenyl group. It is a colorless liquid found together with terpenes in betel oil.

Properties and reactions

Chavicol is miscible with alcohol, ether, and chloroform. Dimerization of chavicol gives the neo-lignan magnolol.

Uses

Chavicol is used as an odorant in perfumery and as a flavor. It is found in many essential oils, including anise and gardenia.{{Cite web|url=http://www.thegoodscentscompany.com/data/rw1015241.html|title = Chavicol, 501-92-8}}

Biosynthesis

Chavicol is formed in sweet basil (Ocimum Basilicum) by the phenylpropanoid pathway via p-coumaryl alcohol. The allylic alcohol in p-coumaryl alcohol is converted into a leaving group. This then leaves thus forming a cation, this cation can be regarded as a quinone methide which then is reduced by NADPH to form either anol or chavicol.{{cite journal | doi = 10.1039/b605407b | title = Chavicol formation in sweet basil (Ocimum basilicum): Cleavage of an esterified C9 hydroxyl group with NAD(P)H-dependent reduction | date = 2006 | last1 = Vassão | first1 = Daniel G. | last2 = Gang | first2 = David R. | last3 = Koeduka | first3 = Takao | last4 = Jackson | first4 = Brenda | last5 = Pichersky | first5 = Eran | last6 = Davin | first6 = Laurence B. | last7 = Lewis | first7 = Norman G. | journal = Org. Biomol. Chem. | volume = 4 | issue = 14 | pages = 2733–2744 | pmid = 16826298 }}

:File:Biosynthesis of chavicol.jpg{{clear-left}}

See also

References