Basic information
- CAS
140-10-3- Standard SMILES
O=C(O)/C=C/c1ccccc1- InChIKey
WBYWAXJHAXSJNI-VOTSOKGWSA-N- Molecular formula
- C9H8O2
- Average molar mass
- 148.16 g/mol
- Monoisotopic mass
- 148.0524295
Overview
Cinnamic acid is a monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia. It has a role as a plant metabolite. It is a member of cinnamic acids and a member of styrenes. It is a conjugate acid of a cinnamate.
Names & identifiers
- Preferred name
- Cinnamic Acid
- IUPAC
- (E)-3-phenylprop-2-enoic acid
- English name
- trans-Cinnamic acid
- Molecular formula
- C9H8O2
- Molecular weight
- 148.16
Names & synonyms
CINNAMIC ACID621-82-93-Phenylacrylic acidPhenylacrylic acidZimtsaeure(E)-3-phenylprop-2-enoic acid3-Phenylpropenoic acid3-phenylprop-2-enoic acidbeta-Phenylacrylic acidCinnamic acid, (E)-Cinnamylic acidBenzenepropenoic acid
Show more names
3-PHENYL-2-PROPENOIC ACIDFEMA 2288(2E)-3-phenylprop-2-enoic acid(E)-Cinnamic acid(e)-2-propenoicaci(E)-3-Phenylacrylic acidTRANS-3-PHENYLACRYLIC ACIDtrans-Cinnamicacid 140-10-3
Benzylideneacetic acidFEMA No. 2288CINNAMIC ACIDUMCinnamic acid, trans-Kyselina skoricoveAcidum cinnamylicumU14A832J8DNSC-9189
Database identifiers
- CAS
140-10-3、621-82-9- PubChem CID
- 444539
- DTXSID
DTXSID5022489- ChEMBL
CHEMBL27246- ChEBI
CHEBI:27386- UNII
- U14A832J8D
- EC Number
- 205-398-1、210-708-3
- Nikkaji
- J2.024I、J2.087G
Properties
Computed structural properties
- XLogP
- 2.1
- Topological polar surface area
- 37.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 155
Experimental & physicochemical properties
Chemical Classes
Other Classes -> Organic Acids
Other Classes -> Organic Acids
SpringerMaterials PropertiesAngular frequency
Fragrances
Fragrance Ingredient (Cinnamic acid) -> IFRA transparency List
Fragrance Ingredient (trans-Cinnamic acid) -> IFRA transparency List
LogP2.13
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility
0.546 mg/mL
insoluble in water; soluble in oils
slightly soluble (in ethanol)
Boiling Point
298.00 to 300.00 °C. @ 760.00 mm Hg
300 °C
Melting Point133 °C
Physical Description
Solid with a honey floral odor; [Merck Index] White crystalline solid; [Alfa Aesar MSDS]
White crystalline powder with a mild odor; [Alfa Aesar MSDS]
Solid
White crystalline scales, honey floral odour
Ionization Efficiency
Positive
1.18
2.7
Agilent XCT
Electrospray ionization
formic acid (5.3nM)
Dissociation Constants4.45
Physicochemical properties
- Melting point
- 133 °C · 133 °C (lit.)
- Boiling point
- 300 °C · 300 °C(lit.)
- Density
- 1.248 · 1.248
- bulk density
- 500 kg/m3 · 500kg/m3
- vapor pressure
- 1.3 hPa · 1.3 hPa (128 °C)
- refractive index
- 1.5049 · 1.5049 (estimate)
- Flash point
- 230 °F · >230 °F
- storage temp.
- 2 · 2-8°C
- solubility
- 0.4 g/l · 0.4g/l
- pka
- 4.44 · 4.44(at 25℃)
- form
- Crystalline Powder
- color
- White to almost white
- Specific Gravity
- 0.91 · 0.91
- Odor
- Faint odour
- PH Range
- 3 · 3 - 4
- PH
- 3 · 3-4 (0.4g/l, H2O, 20℃)
- Odor Type
- balsamic
- biological source
- synthetic
- Water Solubility
- 0.4 g/L · 0.4 g/L (20 ºC)
- λmax
- 273 nm · 273nm(MeOH)(lit.)
- Merck
- 14 · 14,2299
- BRN
- 1905952 · 1905952
- Henry's Law Constant
- 2.8 · 2.8×1011 mol/(m3Pa) at 25℃, Abraham and Jr. (2019)
- Stability
- Light Sensitive
- Major Application
- flavors and fragrances
- Cosmetics Ingredients Functions
- PERFUMINGSKIN CONDITIONING
- InChI
- 1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+
- InChIKey
- WBYWAXJHAXSJNI-VOTSOKGWSA-N
- SMILES
- OC(=O)\C=C\c1ccccc1
- LogP
- 2.13 · 2.130
- CAS DataBase Reference
- 140 · 140-10-3(CAS DataBase Reference)
- FDA UNII
- 14 A832J8D · U14A832J8D
- NIST Chemistry Reference
- Cinnamic acid(140-10-3)
- EPA Substance Registry System
- (E)-Cinnamic acid (140-10-3)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 305 · P305+P351+P338-P261-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36-37/39
- WGK Germany
- 1 · 1
- RTECS
- 7850000 · GD7850000
- TSCA
- TSCA listed
- HS Code
- 29163900 · 29163900
- Storage Class
- 13 · 13 - Non Combustible Solids
- Hazard Classifications
- 2 · Eye Irrit. 2
- Toxicity
- 50 orally · LD50 orally in Rabbit: 2500 mg/kg LD50 dermal Rabbit > 5000 mg/kg
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 97.8% (1644 of 1681) of all reports.
Not Classified
Aggregated GHS information provided per 1681 reports by companies from 7 notifications to the ECHA C&L Inventory.
This chemical does not meet GHS hazard criteria for 76.1% (284 of 373) of all reports.
Warning
H315 (15.5%): Causes skin irritation [Warning Skin corrosion/irritation]
Hazard information
Regulatory Information
Chemical: 2-Propenoic acid, 3-phenyl-, (E)-
Chemical: 2-Propenoic acid, 3-phenyl-
Regulation (EC) No 1831/2003 (amended)
Status: Active Update: 06-02-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/23816
2-Propenoic acid, 3-phenyl-, (E)-: Does not have an individual approval but may be used under an appropriate group standard
Cinnamic acid: Does not have an individual approval but may be used under an appropriate group standard
Other Safety Information
IMAP assessments - Cinnamic acid: Human health tier II assessment
IMAP assessments - Cinnamic acid: Human health tier II assessment
Hazards Summary
A mild skin irritant; Causes gastrointestinal changes in acute oral studies of rats; [RTECS] Safe when used as a flavoring agent in food; [JECFA] An eye irritant; [Alfa Aesar MSDS] See Hydrocinnamic acid.
A mild skin and strong eye irritant; [Alfa Aesar MSDS] See Hydrocinnamic acid.
Hazard Classes and Categories
Skin Irrit. 2 (15.5%)
Not Classified
Toxicology
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- GD7850000
- hs_code
- 29163900
- Toxicity
- LD50 orally in Rabbit: 2500 mg/kg LD50 dermal Rabbit > 5000 mg/kg
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36-37/39
- Storage Class
- 13 - Non Combustible Solids
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Hazard Classifications
- Eye Irrit. 2
- Precautionary statements
- P305+P351+P338-P261-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
Uses & manufacturing
Uses
Occurs in storax, balsam of Peru, oil of cinnamon, and coca leaves (trans isomer); Used as a fragrance and flavoring agent; [Merck Index]
The trans- isomer is found in storax, balsam of Peru, oil of cinnamon, and coca leaves; Used as a fragrance and flavoring agent; [Merck Index] Used in perfumery and as an anthelmintic; [Alfa Aesar MSDS]
Household ProductsInformation on 1 consumer products that contain Cinnamic acid in the following categories is provided:
Use Classification
Fragrance Ingredients
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information
2-Propenoic acid, 3-phenyl-, (2E)-: ACTIVE
2-Propenoic acid, 3-phenyl-: ACTIVE
Applications
Usestrans-Cinnamic acid is used in flavors, synthetic indigo and pharmaceuticals. It is involved in the production of methyl, ethyl and benzyl esters, which is used in the perfume industry. It serves as a precursor to the sweetener aspartame through enzyme-catalyzed amination to phenylalanine. It is a self-inhibitor produced by fungal spores to prevent germination. In addition, it is used to establish phenolic compounds by liquid chromatography, ultraviolet and mass spectrometry. It is utilized as a potential agent, thereby preventing lung tumor cells from metastasizing. Further, it induces intracellular release of calcium ions from the vacuole to the cytoplasm in order to trigger phytotoxicity in cucumber.
Usestrans-Cinnamic acid was used to establish library of phenolic compounds by liquid chromatography/ultraviolet and mass spectrometry/mass spectrometry.
General Descriptiontrans-Cinnamic acid is an α,β-unsaturated aromatic acid that can be used as a flavoring agent. It is mainly used to prepare ester derivatives that are used in perfume industry. trans-Cinnamic acid is the key volatile components of cinnamon essential oil.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
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Additional notes
DefinitionChEBI: Cinnamic acid is a monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia. It has a role as a plant metabolite. It is a member of styrenes and a member of cinnamic acids. It is a conjugate acid of a cinnamate.
Related reactions
649 records
Compound notes
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