Showing Compound Cinnamyl alcohol (FDB000887)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:45 UTC

Update date

2018-05-28 18:41:40 UTC

Primary ID

FDB000887

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Cinnamyl alcohol

Description

Cinnamyl alcohol, also known as 3-phenyl-2-propenol or styrylcarbinol, belongs to the class of organic compounds known as cinnamyl alcohols. These are aromatic alcohols containing a 3-phenylprop-2-en-1-ol moiety. Cinnamyl alcohol is an extremely weak basic (essentially neutral) compound (based on its pKa). Cinnamyl alcohol is a sweet, balsam, and bitter tasting compound. Cinnamyl alcohol is found, on average, in the highest concentration in ceylon cinnamons and star anises. Cinnamyl alcohol has also been detected, but not quantified in, several different foods, such as cornmints, purslanes, oil-seed camellia, sweet rowanberries, and enokitakes. This could make cinnamyl alcohol a potential biomarker for the consumption of these foods.

CAS Number

104-54-1

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
3-Phenyl-2-propen-1-ol	ChEBI
Styrylcarbinol	ChEBI
Zimtalcohol	ChEBI
1-Phenyl-1-propen-3-ol	HMDB
3-Phenyl-2-propene-1-ol	HMDB
3-Phenyl-2-propenol	HMDB
3-Phenylallyl alcohol	HMDB
3-Phenylprop-2-en-1-ol	HMDB
Cinnamic alcohol	HMDB
Cinnamyl alcohol, 8ci	HMDB
FEMA 2294	HMDB
gamma-Phenylallyl alcohol	HMDB
Phenyl-2-propen-1-ol	HMDB
Phenyl-2-propenol	HMDB
Phenylallyl alcohol	HMDB
Styrone	HMDB
Styryl alcohol	HMDB
Cinnamyl alcohol, (e)-isomer	HMDB
Cinnamyl alcohol, titanium (4+) salt	HMDB
(Z)-3-Phenyl-2-propen-1-ol	ChEBI
Cinnamyl alcohol, 8CI	db_source
Z-Cinnamyl alcohol	ChEBI

Predicted Properties

Property	Value	Source
Water Solubility	2.34 g/L	ALOGPS
logP	1.93	ALOGPS
logP	1.82	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	15.62	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	43.19 m³·mol⁻¹	ChemAxon
Polarizability	15.2 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C9H10O

IUPAC name

3-phenylprop-2-en-1-ol

InChI Identifier

InChI=1S/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2

InChI Key

OOCCDEMITAIZTP-UHFFFAOYSA-N

Isomeric SMILES

OCC=CC1=CC=CC=C1

Average Molecular Weight

134.1751

Monoisotopic Molecular Weight

134.073164942

Classification

Description

belongs to the class of organic compounds known as cinnamyl alcohols. These are aromatic alcohols containing a 3-phenylprop-2-en-1-ol moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamyl alcohols

Sub Class

Not Available

Direct Parent

Cinnamyl alcohols

Alternative Parents

Substituents

Cinnamyl alcohol
Styrene
Benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

primary alcohol (CHEBI:17177 )
a small molecule (CINNAMYL-ALC )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Food and nutrition:

Flavoring agent

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 80.56%; H 7.51%; O 11.92%	DFC
Melting Point	33 oC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	1.95	HANSCH,C ET AL. (1995)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uyl-4900000000-f5041423af8993736d98	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-010c-9500000000-c3c6821e801767306100	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0900000000-d61d9fd352f7bed6ae4e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-1900000000-f7dabd1250954bcefeba	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-8900000000-8482f1c6f481aa95c81c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-aee2c26cbb0d652aec2f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900000000-1731b8b6e8d3c392931a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gdl-6900000000-ec41da5c5b1a22a7f9dc	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0900000000-d61d9fd352f7bed6ae4e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-1900000000-f7dabd1250954bcefeba	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-8900000000-8482f1c6f481aa95c81c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-aee2c26cbb0d652aec2f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900000000-1731b8b6e8d3c392931a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gdl-6900000000-ec41da5c5b1a22a7f9dc	JSpectraViewer

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

17177

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB29697

CRC / DFC (Dictionary of Food Compounds) ID

BLR24-Y:BLR24-Y

EAFUS ID

652

Dr. Duke ID

CINNAMIC-ALCOHOL|CINNAMYL-ALCOHOL

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

104-54-1

GoodScent ID

rw1003291

SuperScent ID

5315892

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
allelochemic			DUKE
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	DUKE
anti mutagenic			DUKE
FEMA			DUKE
herbicide	24527	A substance used to destroy plant pests.	DUKE
irritant			DUKE
nematicide	25491	A substance used to destroy pests of the phylum Nematoda (roundworms).	DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
oil	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
hyacinth	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
balsam	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spicy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
green	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
powdery	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cinnamic	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter	Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755

Files

MSDS

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References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Showing Compound Cinnamyl alcohol (FDB000887)

Structure for FDB000887 (Cinnamyl alcohol)