Cinnamyl alcohol

Last updated
Cinnamyl alcohol [1]
Cinnamyl alcohol.svg
CinnamylAlcoholOnPetriDish.jpg
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 InfoCard 100.216.224 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-212-3
KEGG
PubChem CID
UNII
  • InChI=1S/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2/b7-4+ Yes check.svgY
    Key: OOCCDEMITAIZTP-QPJJXVBHSA-N Yes check.svgY
  • 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 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)
Slightly
Solubility soluble in ethanol, acetone, dichloromethane
-87.2·10−6 cm3/mol
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H317
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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 .

Related Research Articles

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<span class="mw-page-title-main">Solvent</span> Substance dissolving a solute resulting in a solution

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<span class="mw-page-title-main">Solubility</span> Capacity of a substance to dissolve in a homogeneous way

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<span class="mw-page-title-main">Potassium hydroxide</span> Inorganic compound (KOH)

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<span class="mw-page-title-main">Precipitation (chemistry)</span> Chemical process leading to the settling of an insoluble solid from a solution

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<span class="mw-page-title-main">Cinnamaldehyde</span> Chemical compound

Cinnamaldehyde is an organic compound with the formula or C₆H₅CH=CHCHO. Occurring naturally as predominantly the trans (E) isomer, it gives cinnamon its flavor and odor. It is a phenylpropanoid that is naturally synthesized by the shikimate pathway. This pale yellow, viscous liquid occurs in the bark of cinnamon trees and other species of the genus Cinnamomum. It is an essential oil. The bark of cinnamon tree contains high concentrations of cinnamaldehyde.

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Cinnamic acid is an organic compound with the formula C6H5-CH=CH-COOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants. It exists as both a cis and a trans isomer, although the latter is more common.

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<span class="mw-page-title-main">Triphenylphosphine</span> Chemical compound

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Pentacene is a polycyclic aromatic hydrocarbon consisting of five linearly-fused benzene rings. This highly conjugated compound is an organic semiconductor. The compound generates excitons upon absorption of ultra-violet (UV) or visible light; this makes it very sensitive to oxidation. For this reason, this compound, which is a purple powder, slowly degrades upon exposure to air and light.

<span class="mw-page-title-main">Silver carbonate</span> Chemical compound

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<span class="mw-page-title-main">Caesium carbonate</span> Chemical compound

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Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is among the simplest aromatic aldehydes and one of the most industrially useful.

<span class="mw-page-title-main">Cinnamyl acetate</span> Chemical compound

Cinnamyl acetate is a chemical compound of the cinnamyl ester family, in which the variable R group is substituted by a methyl group. As a result of the non-aromatic carbon-carbon double bond, cinnamyl acetate can exist in a Z and an E configuration:

<span class="mw-page-title-main">1-Pentadecanol</span> 15-carbon alcohol

1-Pentadecanol is an organic chemical compound classified as an alcohol. At room temperature, it is a white, flaky solid. It is a saturated long-chain fatty alcohol consisting of a pentadecane chain with a hydroxy group as substituent on one end. It is an achiral molecule.

References

  1. Merck Index, 11th Edition, 2305
  2. 1 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