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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

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+

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

1994
149
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Activator
1430
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Molecular and pharmacological analysis of an octopamine receptor from American cockroach and fruit fly in response to plant essential oils.
2005 Jul
High-resolution transcriptional profiling of chemical-stimulated dendritic cells identifies immunogenic contact allergens, but not prohaptens.
2010
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
Development of a new in vitro skin sensitization assay (Epidermal Sensitization Assay; EpiSensA) using reconstructed human epidermis.
2013 Dec
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
Patents

Patents

04021411
3
JPH072627A
3
JPH09194339A
6
JPH10139793A
2
JPH1030055A
2
JPS59196878A
3

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 Fri Dec 15 15:44:54 UTC 2023
Edited
by admin
on Fri Dec 15 15:44:54 UTC 2023
Record UNII
SS8YOP444F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CINNAMYL ALCOHOL
FCC   FHFI   INCI   MI   WHO-DD  
INCI  
Official Name English
CINNAMYL ALCOHOL [INCI]
Common Name English
CINNAMYL ALCOHOL [FHFI]
Common Name English
(E)-3-PHENYL-2-PROPEN-1-OL
Systematic Name English
CINNAMYL ALCOHOL [MI]
Common Name English
STYRYL CARBINOL
Systematic Name English
2-PROPEN-1-OL, 3-PHENYL-
Systematic Name English
(E)-3-PHENYLPROP-2-EN-1-OL
Systematic Name English
CINNAMIC ALCOHOL
Common Name English
NSC-623440
Code English
3-PHENYL-2-PROPEN-1-OL
Systematic Name English
3-HYDROXY-1-PHENYLPROP-1-ENE
Systematic Name English
(E)-CINNAMYL ALCOHOL
Systematic Name English
NSC-8775
Code English
CINNAMYL ALCOHOL (CONSTITUENT OF CINNAMOMUM CASSIA BARK) [DSC]
Common Name English
1-PHENYL-3-HYDROXY-1-PROPENE
Systematic Name English
Cinnamyl alcohol [WHO-DD]
Common Name English
FEMA NO. 2294
Code English
CINNAMYL ALCOHOL (CONSTITUENT OF CINNAMOMUM VERUM BARK) [DSC]
Common Name English
CINNAMYL ALCOHOL [FCC]
Common Name English
TRANS-CINNAMYL ALCOHOL
Systematic Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 40512
Created by admin on Fri Dec 15 15:44:54 UTC 2023 , Edited by admin on Fri Dec 15 15:44:54 UTC 2023
JECFA EVALUATION CINNAMYL ALCOHOL
Created by admin on Fri Dec 15 15:44:54 UTC 2023 , Edited by admin on Fri Dec 15 15:44:54 UTC 2023
CFR 21 CFR 172.151
Created by admin on Fri Dec 15 15:44:54 UTC 2023 , Edited by admin on Fri Dec 15 15:44:54 UTC 2023
NDF-RT N0000185508
Created by admin on Fri Dec 15 15:44:55 UTC 2023 , Edited by admin on Fri Dec 15 15:44:55 UTC 2023
Code System Code Type Description
NDF-RT
N0000175629
Created by admin on Fri Dec 15 15:44:55 UTC 2023 , Edited by admin on Fri Dec 15 15:44:55 UTC 2023
PRIMARY Increased Histamine Release [PE]
DAILYMED
SS8YOP444F
Created by admin on Fri Dec 15 15:44:54 UTC 2023 , Edited by admin on Fri Dec 15 15:44:54 UTC 2023
PRIMARY
NDF-RT
N0000171131
Created by admin on Fri Dec 15 15:44:54 UTC 2023 , Edited by admin on Fri Dec 15 15:44:54 UTC 2023
PRIMARY Allergens [Chemical/Ingredient]
CAS
4407-36-7
Created by admin on Fri Dec 15 15:44:54 UTC 2023 , Edited by admin on Fri Dec 15 15:44:54 UTC 2023
PRIMARY
CAS
104-54-1
Created by admin on Fri Dec 15 15:44:54 UTC 2023 , Edited by admin on Fri Dec 15 15:44:54 UTC 2023
NON-SPECIFIC STEREOCHEMISTRY
ECHA (EC/EINECS)
203-212-3
Created by admin on Fri Dec 15 15:44:54 UTC 2023 , Edited by admin on Fri Dec 15 15:44:54 UTC 2023
PRIMARY
EVMPD
SUB61019
Created by admin on Fri Dec 15 15:44:54 UTC 2023 , Edited by admin on Fri Dec 15 15:44:54 UTC 2023
PRIMARY
FDA UNII
SS8YOP444F
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PRIMARY
DRUG BANK
DB14186
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PRIMARY
NDF-RT
N0000184306
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PRIMARY Cell-mediated Immunity [PE]
PUBCHEM
5315892
Created by admin on Fri Dec 15 15:44:55 UTC 2023 , Edited by admin on Fri Dec 15 15:44:55 UTC 2023
PRIMARY
RXCUI
1362889
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PRIMARY RxNorm
EVMPD
SUB59510
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PRIMARY
CHEBI
33227
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PRIMARY
NSC
623440
Created by admin on Fri Dec 15 15:44:55 UTC 2023 , Edited by admin on Fri Dec 15 15:44:55 UTC 2023
PRIMARY
CHEBI
17177
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PRIMARY
MESH
C020722
Created by admin on Fri Dec 15 15:44:54 UTC 2023 , Edited by admin on Fri Dec 15 15:44:54 UTC 2023
PRIMARY
MERCK INDEX
m3573
Created by admin on Fri Dec 15 15:44:54 UTC 2023 , Edited by admin on Fri Dec 15 15:44:54 UTC 2023
PRIMARY Merck Index
JECFA MONOGRAPH
180
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PRIMARY
HSDB
104-54-1
Created by admin on Fri Dec 15 15:44:54 UTC 2023 , Edited by admin on Fri Dec 15 15:44:54 UTC 2023
PRIMARY
NSC
8775
Created by admin on Fri Dec 15 15:44:55 UTC 2023 , Edited by admin on Fri Dec 15 15:44:55 UTC 2023
PRIMARY
EPA CompTox
DTXSID9041491
Created by admin on Fri Dec 15 15:44:54 UTC 2023 , Edited by admin on Fri Dec 15 15:44:54 UTC 2023
PRIMARY
SMS_ID
100000134260
Created by admin on Fri Dec 15 15:44:55 UTC 2023 , Edited by admin on Fri Dec 15 15:44:55 UTC 2023
PRIMARY
WIKIPEDIA
CINNAMYL ALCOHOL
Created by admin on Fri Dec 15 15:44:55 UTC 2023 , Edited by admin on Fri Dec 15 15:44:55 UTC 2023
PRIMARY
Related Record Type Details
CINNAMON
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
CHINESE CINNAMON
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
CINNAMOMUM CASSIA TWIG
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
Structure of CINNAMYL ALCOHOL
ACTIVE MOIETY
NIH
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