Cinnamyl alcohol

Last updated
Cinnamyl alcohol [1]
Skeletal formula Cinnamyl alcohol.svg
Skeletal formula
A sample of cinnamyl alcohol on a petri dish. CinnamylAlcoholOnPetriDish.jpg
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 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 (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 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]

There is basic medical research investigating the neuroprotective properties of cinnamyl alcohol in terms of the following with respect to epilepsy: [6]

Safety

Cinnamyl alcohol has been found to have a sensitizing effect on some people [7] [8] 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

  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. Monteiro, Álefe Brito; Nunes De Andrade, Humberto Hugo; Da Cruz Guedes, Erika; Ribeiro Portela, Anne Caroline; Oliveira Pires, Hugo Fernandes; Pereira Lopes, Maria Janice; Medeiros Vilar Barbosa, Nayana Maria; Alves, Adriano Francisco; Fernandes De Oliveira Golzio, Adriana Maria; Pergentino De Sousa, Damião; Bezerra Felipe, Cícero Francisco; Nóbrega De Almeida, Reinaldo (2024). "Neuroprotective effect of cinnamic alcohol: A bioactive compound of Cinnamomum spp. essential oil". Neurochemistry International. 179 105807. doi:10.1016/j.neuint.2024.105807. PMID   39069079.
  7. "Food and Chemical Toxicology" (PDF). RIFM. 2007. Archived from the original (PDF) on 2021-01-12. Retrieved 2012-04-05.
  8. Survey and health assessment of chemical substances in massage oils Archived 2007-06-28 at the Wayback Machine