Cinnamyl alcohol
{{chembox
| Watchedfields = changed
| verifiedrevid = 460038749
| Name = Cinnamyl alcohol
| Reference = Merck Index, 11th Edition, 2305
| ImageFile = Cinnamyl alcohol.svg
| ImageName = Skeletal formula
| ImageFile1 = CinnamylAlcoholOnPetriDish.jpg
| ImageName1 = A sample of cinnamyl alcohol on a petri dish.
| PIN = (2E)-3-Phenylprop-2-en-1-ol
| OtherNames = Cinnamyl alcohol
Cinnamic alcohol
Styryl carbinol
Phenylallyl alcohol
Styron[https://books.google.com/books?id=15wEAAAAYAAJ Chemical News and Journal of Industrial Science, Volumes 27-28, Sir William Crookes, page 126]
|Section1={{Chembox Identifiers
| InChI = 1/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2/b7-4+
| InChIKey = OOCCDEMITAIZTP-QPJJXVBHBG
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2/b7-4+
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OOCCDEMITAIZTP-QPJJXVBHSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 4407-36-7
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo1 = 104-54-1
| CASNo1_Comment = (non-specific)
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 33227
| PubChem = 5315892
| EC_number = 203-212-3
| UNII = SS8YOP444F
| UNII_Ref = {{fdacite|correct|FDA}}
| SMILES = c1ccc(cc1)/C=C/CO
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 324794
| ChemSpiderID = 21105870
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C02394
}}
|Section2={{Chembox Properties
| C=9 | H=10 | O=1
| Density = 1.0397 g/cm3 at 35 °C
| MeltingPtC = 33
| BoilingPtC = 250
| Solubility = Slightly
| SolubleOther = soluble in ethanol, acetone, dichloromethane
| MagSus = −87.2·10−6 cm3/mol
}}
|Section7={{Chembox Hazards
| ExternalSDS = [https://fscimage.fishersci.com/msds/51812.htm External MSDS]
| FlashPtC = 126
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|317}}
| PPhrases = {{P-phrases|261|272|280|302+352|321|333+313|363|501}}
}}
|Section8={{Chembox Related
| OtherCompounds = Cinnamic acid; Cinnamaldehyde}}
}}
Cinnamyl alcohol or styron is an organic compound that is found in esterified form in storax, Balsam of Peru, and cinnamon leaves. It forms a white crystalline solid when pure, or a yellow oil when even slightly impure. It can be produced by the hydrolysis of storax.
Cinnamyl alcohol occurs naturally only in small quantities, so its industrial demand is usually fulfilled by chemical synthesis starting from cinnamaldehyde.{{cite journal|last1=Zucca|first1=P|last2=Littarru|first2=M|last3=Rescigno|first3=A|last4=Sanjust|first4=E|title=Cofactor recycling for selective enzymatic biotransformation of cinnamaldehyde to cinnamyl alcohol.|journal=Bioscience, Biotechnology, and Biochemistry|date=May 2009|volume=73|issue=5|pages=1224–6|pmid=19420690|doi=10.1271/bbb.90025|s2cid=28741979|doi-access=free}}
Properties
The compound is a solid at room temperature, forming colorless crystals that melt upon gentle heating. As is typical of most higher-molecular weight alcohols, it is sparingly soluble in water at room temperature, but highly soluble in most common organic solvents.
Uses
Cinnamyl alcohol has a distinctive odor described as "sweet, balsam, hyacinth, spicy, green, powdery, cinnamic" and is used in perfumery{{cite web|url=http://www.thegoodscentscompany.com/data/rw1003291.html|title=cinnamyl alcohol 104-54-1|work=thegoodscentscompany.com|accessdate=26 July 2015}} and as a deodorant.
Cinnamyl alcohol is the starting material used in the synthesis of reboxetine.{{cite web | url = https://www.chemdrug.com/article/8/3284/16419807.html | title = Reboxetine mesilate }}
Safety
Cinnamyl alcohol has been found to have a sensitizing effect on some people{{cite web|title=Food and Chemical Toxicology|url=http://www.rifm.org/doc/Food%20%26%20Chem%20Tox%20RIFM%20Spec%20Suppl%20122007.pdf|year=2007|publisher=RIFM|access-date=2012-04-05|archive-date=2021-01-12|archive-url=https://web.archive.org/web/20210112105000/https://www.rifm.org/doc/Food%20%26%20Chem%20Tox%20RIFM%20Spec%20Suppl%20122007.pdf|url-status=dead}}[http://www2.mst.dk/udgiv/publications/2006/87-7052-278-2/html/kap07_eng.htm Survey and health assessment of chemical substances in massage oils] {{webarchive|url=https://web.archive.org/web/20070628145403/http://www2.mst.dk/udgiv/publications/2006/87-7052-278-2/html/kap07_eng.htm |date=2007-06-28 }} and as a result is the subject of a [https://web.archive.org/web/20150325103119/http://www.ifraorg.org/view_document.aspx?docId=23164 Restricted Standard] issued by [https://web.archive.org/web/20141022122558/http://www.ifraorg.org/en-us/home/public_home IFRA] (International Fragrance Association).
Glycosides
Rosarin and rosavin are cinnamyl alcohol glycosides isolated from Rhodiola rosea.
References
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