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 is a 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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Names


Preferred IUPAC name (2E)-3-Phenylprop-2-en-1-ol
Other names Cinnamyl alcohol Cinnamic alcohol Styryl carbinol Phenylallyl alcohol Styron^[2]
Identifiers
CAS Number	4407-36-7^Y 104-54-1 (non-specific)^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:33227^Y
ChEMBL	ChEMBL324794^Y
ChemSpider	21105870^Y
ECHA InfoCard	100.216.224
EC Number	203-212-3
KEGG	C02394^Y
PubChem CID	5315892
UNII	SS8YOP444F^Y
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+^Y Key: OOCCDEMITAIZTP-QPJJXVBHSA-N^Y 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). Y verify (what is ^YN ?) Infobox references