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Cinnamyl alcohol

From Wikipedia, the free encyclopedia
Cinnamyl alcohol[1]
Skeletal formula
Skeletal formula
A sample of cinnamyl alcohol on a petri dish.
A sample of cinnamyl alcohol on a petri dish.
Names
Preferred IUPAC name
(2E)-3-Phenylprop-2-en-1-ol
Other names
Cinnamyl alcohol
Cinnamic alcohol
Styryl carbinol
Phenylallyl alcohol
Styron[2]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.216.224Edit this at Wikidata
EC Number
  • 203-212-3
KEGG
UNII
  • InChI=1S/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2/b7-4+ checkY
    Key: OOCCDEMITAIZTP-QPJJXVBHSA-N checkY
  • InChI=1/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2/b7-4+
    Key: OOCCDEMITAIZTP-QPJJXVBHBG
  • c1ccc(cc1)/C=C/CO
Properties
C9H10O
Molar mass134.178 g·mol−1
Density1.0397 g/cm3 at 35 °C
Melting point33 °C (91 °F; 306 K)
Boiling point250 °C (482 °F; 523 K)
Slightly
Solubilitysoluble inethanol,acetone,dichloromethane
−87.2·10−6 cm3/mol
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H317
P261,P272,P280,P302+P352,P321,P333+P313,P363,P501
Flash point126 °C (259 °F; 399 K)
Safety data sheet (SDS)External MSDS
Related compounds
Related compounds
Cinnamic acid;Cinnamaldehyde
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Cinnamyl alcohol orstyron[2] is anorganic compound that is found inesterified form instorax,Balsam of Peru, andcinnamon leaves. It forms a white crystalline solid when pure, or a yellow oil when even slightly impure. It can be produced by thehydrolysis of storax.

Cinnamyl alcohol occurs naturally only in small quantities, so its industrial demand is usually fulfilled by chemical synthesis starting fromcinnamaldehyde.[3]

Properties

[edit]

The compound is a solid at room temperature, forming colorless crystals that melt upon gentle heating. As is typical of most higher-molecular weightalcohols, it is sparingly soluble in water at room temperature, but highly soluble in most common organic solvents.

Uses

[edit]

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 ofreboxetine.[5]

Safety

[edit]

Cinnamyl alcohol has been found to have asensitizing effect on some people[6][7] and as a result is the subject of aRestricted Standard issued byIFRA (International Fragrance Association).

Glycosides

[edit]

Rosarin androsavin are cinnamyl alcohol glycosides isolated fromRhodiola rosea.

References

[edit]
  1. ^Merck Index, 11th Edition,2305
  2. ^abChemical 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. Retrieved26 July 2015.
  5. ^"Reboxetine mesilate".
  6. ^"Food and Chemical Toxicology"(PDF). RIFM. 2007. Archived fromthe original(PDF) on 2021-01-12. Retrieved2012-04-05.
  7. ^Survey and health assessment of chemical substances in massage oilsArchived 2007-06-28 at theWayback Machine
Authority control databases: NationalEdit this at Wikidata
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