Grundinformationen
- Standard-SMILES
O=C(O)/C=C/c1ccccc1- InChIKey
WBYWAXJHAXSJNI-VOTSOKGWSA-N- Summenformel
- C9H8O2
- Durchschnittliche Molmasse
- 148,16 g/mol
- Monoisotopische Masse
- 148,0524295
Überblick
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.
Namen und Bezeichner
- Bevorzugter Name
- Cinnamic Acid
- IUPAC
- (E)-3-phenylprop-2-enoic acid
- Lokaler Name
- trans-zimtsure
- Englischer Name
- trans-Cinnamic acid
- Summenformel
- C9H8O2
- Molmasse
- 148.16
Namen und Synonyme
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
Weitere Namen anzeigen
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
Datenbank-Bezeichner
- 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
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,1
- Polarare Oberfläche (TPSA)
- 37,3 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 11
- Formalladung
- 0
- Komplexität
- 155
Experimentelle und physikochemische Eigenschaften
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
Physikochemische Eigenschaften
- Schmelzpunkt
- 133 °C · 133 °C (lit.)
- Siedepunkt
- 300 °C · 300 °C(lit.)
- Dichte
- 1.248 · 1.248
- Dampfdruck
- 1.3 hPa · 1.3 hPa (128 °C)
- Brechungsindex
- 1.5049 · 1.5049 (estimate)
- Flammpunkt
- 230 °F · >230 °F
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- 0.4 g/l · 0.4g/l
- pka
- 4.44 · 4.44(at 25℃)
- Aggregatzustand
- Crystalline Powder
- Farbe
- White to almost white
- Wichte
- 0.91 · 0.91
- Geruch (Odor)
- Faint odour
- PH
- 3 · 3-4 (0.4g/l, H2O, 20℃)
- Geruchsart
- balsamic
- Biologische Quelle
- synthetic
- Wasserlöslichkeit
- 0.4 g/L · 0.4 g/L (20 ºC)
- Merck
- 14 · 14,2299
- BRN
- 1905952 · 1905952
- Henry's Law Constant
- 2.8 · 2.8×1011 mol/(m3Pa) at 25℃, Abraham and Jr. (2019)
- Stabilität
- Light Sensitive
- Major Application
- flavors and fragrances
- Kosmetik-Inhaltsstoffe Funktionen
- 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 Datenbank
- 140 · 140-10-3(CAS DataBase Reference)
- NIST chemische Informationen
- Cinnamic acid(140-10-3)
- EPA chemische Informationen
- (E)-Cinnamic acid (140-10-3)
Sicherheit und Regulatorisches
GHS-Klassifizierung
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]
Gefahrenhinweise
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
Toxikologische Informationen
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Sicherheitsdaten
- wgk
- 1
- tsca
- TSCA listed
- hs_code
- 29163900
- RTECS-Nr.
- GD7850000
- risk_code
- 36/37/38
- Toxizität
- LD50 orally in Rabbit: 2500 mg/kg LD50 dermal Rabbit > 5000 mg/kg
- hazard_code
- Xi
- safety_code
- 26-36-37/39
- Speicherklasse
- 13 - Non Combustible Solids
- Hazard Classifications
- Eye Irrit. 2
Chemie und Industrie
Pharmakologische Informationen
Cellular LocationsMembrane
Verwendung und Herstellung
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
Anwendungen
BeschreibungDie trans-3-Phenylacrylsäure bildet farblose, wenig wasserlösliche Blättchen. Die Säure kommt in frei und verestert in verschiedenen etherischen Ölen und Harzen vor. Technisch stellt man aus der Säure eine Vielzahl von Estern her, die in der Parfümindustrie ausgedehnte Verwendung finden.
Verwendentrans-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.
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Ergänzende Hinweise
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.
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