Record Information
Creation date2015-10-09 22:28:50 UTC
Update date2017-01-19 02:36:14 UTC
FoodComEx IDPC000148
FoodDB RecordFDB008784
Chemical Information
Nametrans-Cinnamic acid
DescriptionTrans-cinnamic acid, also known as (e)-cinnamic acid or phenylacrylic acid, belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. Cinnamic acid can exist in both the cis and trans form, with the trans-form being most common. Trans-cinnamic acid is a weakly acidic compound (based on its pKa). It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Trans-cinnamic acid occurs naturally in a number of plants. It is a sweet, balsam, or cinnamon tasting compound. Trans-cinnamic acid is characterized by a honey-like odor. Trans-cinnamic acid is found in a number of foods with the highest concentration found in chinese cinnamons (cinnamon bark), olives, and lingonberries and in a lower concentration in redcurrants, red raspberries, and corianders. Trans-cinnamic acid has also been detected, but not quantified in common oregano, pepper (spice), fennels, pomegranates, and european cranberries. Trans-cinnamic acid has also been shown to be a microbial metabolite as it is produced by microbes belonging to the Alcaligenes, Brevibacterium, Cellulomonas, and Pseudomonas families (PMID: 16349793). In plants, cinnamic acid is a central intermediate in the biosynthesis of myriad natural products include lignols (precursors to lignin and lignocellulose), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. Its biosynthesis involves the action of the enzyme phenylalanine ammonia-lyase (PAL) on phenylalanine (PMID:20035037). Cinnamic acid is used in flavorings, the production of synthetic indigo, and certain pharmaceuticals. A major use of trans-cinnamic acid is as a precursor to produce methyl cinnamate, ethyl cinnamate, and benzyl cinnamate for the perfume industry.
CAS Number140-10-3
(2E)-2-Phenyl-2-propenoic acidbiospider
(2E)-3-Phenyl-2-Propenoic acidbiospider
(2e)-3-Phenylacrylic acidChEBI
(E)-3-Phenyl-2-propenoic acidbiospider
(E)-3-Phenylacrylic acidbiospider
(E)-3-Phenylprop-2-enoic acidbiospider
(E)-Cinnamic acidbiospider
2-Propenoic acid, 3-phenyl-, (E)-biospider
Cinnamic acid, (E)-biospider
trans-3-Phenyl-2-propenoic acidbiospider
trans-3-Phenylacrylic acidbiospider
trans-Cinnamic acidbiospider
Chemical FormulaC9H8O2
IUPAC name(2E)-3-phenylprop-2-enoic acid
InChI IdentifierInChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+
Isomeric SMILESOC(=O)\C=C\C1=CC=CC=C1
Average Molecular Weight148.1586
Monoisotopic Molecular Weight148.0524295
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassCinnamic acids
Direct ParentCinnamic acids
Alternative Parents
  • Cinnamic acid
  • Styrene
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Experimental logP2.13HANSCH,C ET AL. (1995)
Experimental Water Solubility0.546 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting PointMp 133°DFC
Foods of Origin
FoodContent Range AverageReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 1 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez
Commercial Vendors
AKSci D023
AKSci J40063
AKSci J92858