Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C9H10O |
| Molecular Weight | 134.1751 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC\C=C/C1=CC=CC=C1
InChI
InChIKey=OOCCDEMITAIZTP-DAXSKMNVSA-N
InChI=1S/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2/b7-4-
| Molecular Formula | C9H10O |
| Molecular Weight | 134.1751 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
http://www.inchem.org/documents/jecfa/jecmono/v46je07.htm
http://onlinelibrary.wiley.com/doi/10.1002/0471238961.0309141405091205.a01/abstract
https://www.ncbi.nlm.nih.gov/pubmed/15811570
https://www.ncbi.nlm.nih.gov/pubmed/23178275
Curator's Comment: description was created based on several sources, including
http://www.inchem.org/documents/jecfa/jecmono/v46je07.htm
http://onlinelibrary.wiley.com/doi/10.1002/0471238961.0309141405091205.a01/abstract
https://www.ncbi.nlm.nih.gov/pubmed/15811570
https://www.ncbi.nlm.nih.gov/pubmed/23178275
Cinnamyl alcohol (CAL, 3-phenyl-2-propen-1-ol) is found mostly in esterized form as a natural component in cinnamon oil obtained from the bark of the Cylonese cinnamon tree. Furthermore, (esterized) CAL is a component of the balsam of Peru from Myroxylon pereirae, of Styrax (balsam) from the wood of Liquidambar orientalis Miller or Liquidambar styraciflua L. and further plant extracts. The regulatory status of CAL includes approval (21 CFR 172.515) by the FDA and Generally Recognized as Safe (GRAS) as flavor ingredient [Number 2294] by the Flavor and Extract Manufacturers Association. CAL included in the Council of Europes list of substances which may be used in foodstuffs. CAL have been reported as common component of food occurring mainly in a wide variety of fruits, vegetables, and spices in varying concentrations. The plant phenolic CAL is used as a fragrance ingredient and has antipyretic and antiproliferative effects. A recent report also demonstrated its vasodilatory activity.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Dual regulation of skin sensitizer-induced HMOX1 expression by Bach1 and Nrf2: Comparison to regulation of the AKR1C2-ARE element in the KeratinoSens cell line. | 2015-11-01 |
|
| Chemical allergens stimulate human epidermal keratinocytes to produce lymphangiogenic vascular endothelial growth factor. | 2015-03-01 |
|
| Development of a new in vitro skin sensitization assay (Epidermal Sensitization Assay; EpiSensA) using reconstructed human epidermis. | 2013-12 |
|
| NCTC 2544 and IL-18 production: a tool for the identification of contact allergens. | 2013-04 |
|
| Development of an in vitro dendritic cell-based test for skin sensitizer identification. | 2013-03-18 |
|
| Differentiation of skin sensitizers from irritant chemicals by interleukin-1α and macrophage inflammatory protein-2 in murine keratinocytes. | 2013-01-10 |
|
| Cinnamyl alcohol attenuates vasoconstriction by activation of K⁺ channels via NO-cGMP-protein kinase G pathway and inhibition of Rho-kinase. | 2012-12-31 |
|
| B cell increases and ex vivo IL-2 production as secondary endpoints for the detection of sensitizers in non-radioisotopic local lymph node assay using flow cytometry. | 2012-03-25 |
|
| An in vitro test to screen skin sensitizers using a stable THP-1-derived IL-8 reporter cell line, THP-G8. | 2011-12 |
|
| The intra- and inter-laboratory reproducibility and predictivity of the KeratinoSens assay to predict skin sensitizers in vitro: results of a ring-study in five laboratories. | 2011-04 |
|
| Effects of cinnamaldehyde on the glucose transport activity of GLUT1. | 2011-02 |
|
| Keratinocyte gene expression profiles discriminate sensitizing and irritating compounds. | 2010-09 |
|
| High-resolution transcriptional profiling of chemical-stimulated dendritic cells identifies immunogenic contact allergens, but not prohaptens. | 2010 |
|
| Molecular and pharmacological analysis of an octopamine receptor from American cockroach and fruit fly in response to plant essential oils. | 2005-07 |
|
| Fragrance material review on cinnamyl alcohol. | 2005-06 |
|
| Human skin absorption and metabolism of the contact allergens, cinnamic aldehyde, and cinnamic alcohol. | 2000-11-01 |
|
| Penetration of the fragrance compounds, cinnamaldehyde and cinnamyl alcohol, through human skin in vitro. | 1989-03 |
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Dermal systemic exposure in cosmetic products (http://fragrancematerialsafetyresource.elsevier.com/sites/default/files//GS5-cinnamyl_alcohol.pdf)
0.0416 mg/kg/day
Route of Administration:
Transdermal
The abdominal skin samples were stripped of their adipose tissue, giving a skin membrane of epidermis and dermis of a thikness of aproximately 2mm. Before application of cinnamyl alcohol the skin was allowed to equilibrate in the glass diffusion cells for 24 h. 250 ul of cinnamyl alcohol (200 mg/ml in ethanol) was placed on the epidermal side of the skin. The permeability coefficients was calculated to be 6.9*10^-5 cm/h.
| Substance Class |
Chemical
Created
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admin
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Edited
Mon Mar 31 22:50:07 GMT 2025
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| Record UNII |
OT636Q443X
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| Record Status |
Validated (UNII)
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| Record Version |
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