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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
Structure of CINNAMYL ALCOHOL, (Z)-

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-

HIDE SMILES / InChI

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

Description
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

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Penetration of the fragrance compounds, cinnamaldehyde and cinnamyl alcohol, through human skin in vitro.
1989 Mar
Molecular and pharmacological analysis of an octopamine receptor from American cockroach and fruit fly in response to plant essential oils.
2005 Jul
Effects of cinnamaldehyde on the glucose transport activity of GLUT1.
2011 Feb
Cinnamyl alcohol attenuates vasoconstriction by activation of K⁺ channels via NO-cGMP-protein kinase G pathway and inhibition of Rho-kinase.
2012 Dec 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 Mar 25
Patents

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
In Vitro Use Guide
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
by admin
on Sat Dec 16 09:46:14 GMT 2023
Edited
by admin
on Sat Dec 16 09:46:14 GMT 2023
Record UNII
OT636Q443X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CINNAMYL ALCOHOL, (Z)-
Systematic Name English
2-PROPEN-1-OL, 3-PHENYL-, (2Z)-
Systematic Name English
2-PROPEN-1-OL, 3-PHENYL-, (Z)-
Systematic Name English
(Z)-3-PHENYL-2-PROPEN-1-OL
Systematic Name English
(Z)-CINNAMYL ALCOHOL
Systematic Name English
CIS-CINNAMYL ALCOHOL
Systematic Name English
Code System Code Type Description
CAS
4510-34-3
Created by admin on Sat Dec 16 09:46:14 GMT 2023 , Edited by admin on Sat Dec 16 09:46:14 GMT 2023
PRIMARY
CHEBI
33226
Created by admin on Sat Dec 16 09:46:14 GMT 2023 , Edited by admin on Sat Dec 16 09:46:14 GMT 2023
PRIMARY
FDA UNII
OT636Q443X
Created by admin on Sat Dec 16 09:46:14 GMT 2023 , Edited by admin on Sat Dec 16 09:46:14 GMT 2023
PRIMARY
PUBCHEM
5280511
Created by admin on Sat Dec 16 09:46:14 GMT 2023 , Edited by admin on Sat Dec 16 09:46:14 GMT 2023
PRIMARY