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Showing Compound Cinnamyl alcohol (FDB000887)

Record Information
Version1.0
Creation date2010-04-08 22:04:45 UTC
Update date2019-11-26 02:55:35 UTC
Primary IDFDB000887
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCinnamyl alcohol
DescriptionCinnamyl alcohol, also known as styrylcarbinol or zimtalcohol, 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 a sweet, balsam, and bitter tasting compound. Cinnamyl alcohol is found, on average, in the highest concentration within ceylon cinnamons (Cinnamomum verum) and star anises (Illicium verum). Cinnamyl alcohol has also been detected, but not quantified in, several different foods, such as green zucchinis (Cucurbita pepo var. cylindrica), turmerics (Curcuma longa), shiitakes (Lentinus edodes), bamboo shoots (Phyllostachys edulis), and pepper (spice). This could make cinnamyl alcohol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Cinnamyl alcohol.
CAS Number104-54-1
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
3-Phenyl-2-propen-1-olChEBI
StyrylcarbinolChEBI
ZimtalcoholChEBI
3-Phenyl-2-propene-1-olMeSH
Cinnamic alcoholMeSH
Cinnamyl alcohol, (e)-isomerMeSH
Cinnamyl alcohol, titanium (4+) saltMeSH
1-Phenyl-1-propen-3-olHMDB
3-Phenyl-2-propenolHMDB
3-Phenylallyl alcoholHMDB
3-Phenylprop-2-en-1-olHMDB, MeSH
Cinnamyl alcohol, 8ciHMDB
FEMA 2294HMDB
gamma-Phenylallyl alcoholHMDB
Phenyl-2-propen-1-olHMDB
Phenyl-2-propenolHMDB
Phenylallyl alcoholHMDB
StyroneHMDB
Styryl alcoholHMDB
(Z)-3-Phenyl-2-propen-1-olChEBI
Cinnamyl alcohol, 8CIdb_source
Z-Cinnamyl alcoholChEBI
Predicted Properties
PropertyValueSource
Water Solubility2.34 g/LALOGPS
logP1.93ALOGPS
logP1.82ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)15.62ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.19 m³·mol⁻¹ChemAxon
Polarizability15.2 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H10O
IUPAC name3-phenylprop-2-en-1-ol
InChI IdentifierInChI=1S/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2
InChI KeyOOCCDEMITAIZTP-UHFFFAOYSA-N
Isomeric SMILESOCC=CC1=CC=CC=C1
Average Molecular Weight134.1751
Monoisotopic Molecular Weight134.073164942
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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamyl alcohols
Sub ClassNot Available
Direct ParentCinnamyl 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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 80.56%; H 7.51%; O 11.92%DFC
Melting Point33 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP1.95HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCinnamyl alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0uyl-4900000000-f5041423af8993736d98Spectrum
Predicted GC-MSCinnamyl alcohol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-010c-9500000000-c3c6821e801767306100Spectrum
Predicted GC-MSCinnamyl alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCinnamyl alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0900000000-d61d9fd352f7bed6ae4e2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1900000000-f7dabd1250954bcefeba2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-8900000000-8482f1c6f481aa95c81c2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-aee2c26cbb0d652aec2f2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-1731b8b6e8d3c392931a2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gdl-6900000000-ec41da5c5b1a22a7f9dc2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0900000000-d61d9fd352f7bed6ae4e2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1900000000-f7dabd1250954bcefeba2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-8900000000-8482f1c6f481aa95c81c2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-aee2c26cbb0d652aec2f2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-1731b8b6e8d3c392931a2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gdl-6900000000-ec41da5c5b1a22a7f9dc2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1900000000-27dd5aba23f62a0bb7742021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gbc-3900000000-3b0e7fa691549cea10172021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016r-9200000000-ce8637df94824e2a6ed62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014l-4900000000-2cab5f77bd64078bc3f82021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9600000000-06cea44318e246044cfd2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9100000000-e07a9637961c556fc4c52021-09-24View Spectrum
NMRNot Available
ChemSpider ID4444146
ChEMBL IDCHEMBL118958
KEGG Compound IDC02394
Pubchem Compound ID5280511
Pubchem Substance IDNot Available
ChEBI ID17177
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB29697
CRC / DFC (Dictionary of Food Compounds) IDBLR24-Y:BLR24-Y
EAFUS ID652
Dr. Duke IDCINNAMIC-ALCOHOL|CINNAMYL-ALCOHOL
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID104-54-1
GoodScent IDrw1003291
SuperScent ID5315892
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
AllelochemicA chemical released by plants that interacts with other organisms, influencing their behavior or growth. Its biological role involves plant defense and communication. Therapeutically, allelochemics have anti-inflammatory, antimicrobial, and antioxidant properties, with applications in managing anxiety, pain, and infections, as well as potential anticancer uses.DUKE
Allergenic50904 A substance that triggers an immune response, causing allergic reactions. Its biological role is to stimulate the immune system, but it has no therapeutic applications. Key medical uses include diagnosing allergies and developing immunotherapies to desensitize patients to specific allergens, reducing the risk of severe reactions.DUKE
Anti-mutagenicAn agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.DUKE
FEMAA flavoring agent, FEMA (Federation of European Manufacturers of Acetic Acid) is not directly related to biological roles or medical uses. However, as a flavoring agent, it has various applications in the food industry.DUKE
Herbicide24527 A chemical agent that kills or inhibits plant growth, used in agriculture to control weeds and pests. It has no direct biological role or therapeutic applications in human medicine, but its development has led to the creation of related compounds with potential medical uses, such as anticancer agents.DUKE
IrritantAn agent that causes slight inflammation or discomfort, stimulating a biological response. Therapeutically, it can be used to increase blood flow or stimulate healing. Key medical uses include treating wounds, skin conditions, and respiratory issues, such as congestion, by inducing a mild inflammatory response to promote recovery.DUKE
Nematicide25491 An agent that kills nematodes, a type of parasitic worm, used to control infestations in crops and animals, with therapeutic applications in veterinary medicine to treat parasitic infections and promote livestock health.DUKE
Perfumery48318 The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
oil
  1. 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
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
balsam
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spicy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
green
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
powdery
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cinnamic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter
  1. 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
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).