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-QPJJXVBHSA-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 |
|---|---|---|
| Penetration of the fragrance compounds, cinnamaldehyde and cinnamyl alcohol, through human skin in vitro. | 1989 Mar |
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| Human skin absorption and metabolism of the contact allergens, cinnamic aldehyde, and cinnamic alcohol. | 2000 Nov 1 |
|
| Molecular and pharmacological analysis of an octopamine receptor from American cockroach and fruit fly in response to plant essential oils. | 2005 Jul |
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| Fragrance material review on cinnamyl alcohol. | 2005 Jun |
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| High-resolution transcriptional profiling of chemical-stimulated dendritic cells identifies immunogenic contact allergens, but not prohaptens. | 2010 |
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| Keratinocyte gene expression profiles discriminate sensitizing and irritating compounds. | 2010 Sep |
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| Effects of cinnamaldehyde on the glucose transport activity of GLUT1. | 2011 Feb |
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| Cinnamyl alcohol attenuates vasoconstriction by activation of K⁺ channels via NO-cGMP-protein kinase G pathway and inhibition of Rho-kinase. | 2012 Dec 31 |
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| NCTC 2544 and IL-18 production: a tool for the identification of contact allergens. | 2013 Apr |
|
| Development of a new in vitro skin sensitization assay (Epidermal Sensitization Assay; EpiSensA) using reconstructed human epidermis. | 2013 Dec |
|
| Differentiation of skin sensitizers from irritant chemicals by interleukin-1α and macrophage inflammatory protein-2 in murine keratinocytes. | 2013 Jan 10 |
|
| Development of an in vitro dendritic cell-based test for skin sensitizer identification. | 2013 Mar 18 |
|
| Chemical allergens stimulate human epidermal keratinocytes to produce lymphangiogenic vascular endothelial growth factor. | 2015 Mar 1 |
|
| 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 Nov 1 |
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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| Record UNII |
SS8YOP444F
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Validated (UNII)
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EPA PESTICIDE CODE |
40512
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JECFA EVALUATION |
CINNAMYL ALCOHOL
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CFR |
21 CFR 172.151
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NDF-RT |
N0000185508
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N0000175629
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PRIMARY | Increased Histamine Release [PE] | ||
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SS8YOP444F
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PRIMARY | |||
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N0000171131
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PRIMARY | Allergens [Chemical/Ingredient] | ||
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4407-36-7
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104-54-1
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NON-SPECIFIC STEREOCHEMISTRY | |||
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203-212-3
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SUB61019
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SS8YOP444F
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DB14186
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N0000184306
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PRIMARY | Cell-mediated Immunity [PE] | ||
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5315892
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1362889
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SUB59510
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33227
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623440
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17177
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C020722
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DTXSID301314144
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m3573
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180
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104-54-1
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8775
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100000134260
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CINNAMYL ALCOHOL
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ACTIVE MOIETY |
