Cinnamyl alcohol

Cinnamyl alcohol^[1]
Names
	Preferred IUPAC name (2E)-3-Phenylprop-2-en-1-ol
	Other names Cinnamyl alcohol; Cinnamic alcohol; Styryl carbinol; Phenylallyl alcohol; Styron
Identifiers
CAS Number	4407-36-7 ; 104-54-1 (non-specific) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:33227 ;
ChEMBL	ChEMBL324794 ;
ChemSpider	21105870 ;
ECHA InfoCard	100.216.224
EC Number	203-212-3;
KEGG	C02394 ;
PubChem CID	5315892;
UNII	SS8YOP444F ;
CompTox Dashboard (EPA)	DTXSID301314144 ;
	InChI InChI=1S/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2/b7-4+ Key: OOCCDEMITAIZTP-QPJJXVBHSA-N ; InChI=1/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2/b7-4+ Key: OOCCDEMITAIZTP-QPJJXVBHBG;
	SMILES c1ccc(cc1)/C=C/CO;
Properties
Chemical formula	C9H10O
Molar mass	134.178 g·mol−1
Density	1.0397 g/cm3 at 35 °C
Melting point	33 °C (91 °F; 306 K)
Boiling point	250 °C (482 °F; 523 K)
Solubility in water	Slightly
Solubility	soluble in ethanol, acetone, dichloromethane
Magnetic susceptibility (χ)	-87.2·10−6 cm3/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H317
Precautionary statements	P261, P272, P280, P302+P352, P321, P333+P313, P363, P501
Flash point	126°C
Safety data sheet (SDS)	External MSDS
Related compounds
Related compounds	Cinnamic acid; Cinnamaldehyde
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Cinnamyl alcohol or styron^[2] 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.^[3]

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^[4] and as a deodorant.

Cinnamyl alcohol is the starting material used in the synthesis of reboxetine.^[5]

Safety

Cinnamyl alcohol has been found to have a sensitizing effect on some people^[6]^[7] and as a result is the subject of a Restricted Standard issued by IFRA (International Fragrance Association).

Glycosides

Rosarin and rosavin are cinnamyl alcohol glycosides isolated from Rhodiola rosea.

References

^ Merck Index, 11th Edition, 2305
^ ^a ^b Chemical News and Journal of Industrial Science, Volumes 27-28, Sir William Crookes, page 126
^ Zucca, P; Littarru, M; Rescigno, A; Sanjust, E (May 2009). "Cofactor recycling for selective enzymatic biotransformation of cinnamaldehyde to cinnamyl alcohol". Bioscience, Biotechnology, and Biochemistry. 73 (5): 1224–6. doi:10.1271/bbb.90025. PMID 19420690. S2CID 28741979.
^ "cinnamyl alcohol 104-54-1". thegoodscentscompany.com. Retrieved 26 July 2015.
^ "Reboxetine mesilate".
^ "Food and Chemical Toxicology" (PDF). RIFM. 2007. Archived from the original (PDF) on 2021-01-12. Retrieved 2012-04-05.
^ Survey and health assessment of chemical substances in massage oils Archived 2007-06-28 at the Wayback Machine

[1] Merck Index, 11th Edition, 2305

[Crookes-2] Chemical News and Journal of Industrial Science, Volumes 27-28, Sir William Crookes, page 126

[3] Zucca, P; Littarru, M; Rescigno, A; Sanjust, E (May 2009). "Cofactor recycling for selective enzymatic biotransformation of cinnamaldehyde to cinnamyl alcohol". Bioscience, Biotechnology, and Biochemistry. 73 (5): 1224–6. doi:10.1271/bbb.90025. PMID 19420690. S2CID 28741979.

[4] "cinnamyl alcohol 104-54-1". thegoodscentscompany.com. Retrieved 26 July 2015.

[5] "Reboxetine mesilate".

[6] "Food and Chemical Toxicology" (PDF). RIFM. 2007. Archived from the original (PDF) on 2021-01-12. Retrieved 2012-04-05.

[7] Survey and health assessment of chemical substances in massage oils Archived 2007-06-28 at the Wayback Machine

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