Grundinformationen
- Standard-SMILES
O=C(O)/C=C/c1ccc(O)cc1- InChIKey
NGSWKAQJJWESNS-ZZXKWVIFSA-N- Summenformel
- C9H8O3
- Durchschnittliche Molmasse
- 164,16 g/mol
- Monoisotopische Masse
- 164,04734412
Überblick
4-coumaric acid is a coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring. It has a role as a plant metabolite. It is a conjugate acid of a 4-coumarate.
Namen und Bezeichner
- Bevorzugter Name
- P-Coumaric Acid
- IUPAC
- (E)-3-(4-hydroxyphenyl)prop-2-enoic acid
- Englischer Name
- p-Coumaric acid
- Summenformel
- C9H8O3
- Molmasse
- 164.16
Namen und Synonyme
p-coumaric acidtrans-p-Coumaric acidHydroxycinnamic acidPara-Coumaric acidNaringeninic acid(E)-p-Coumaric acidtrans-4-coumaric acidtrans-p-Hydroxycinnamic acidtrans-p-Coumarinic acid4'-hydroxycinnamic acid(E)-p-Hydroxycinnamic acid2-propenoic acid, 3-(4-hydroxyphenyl)-, (2E)-
Weitere Namen anzeigen
(E)-3-(4-hydroxyphenyl)acrylic acidp-CouMaricTRANS-4-HYDROXYCINNAMIC ACIDP-CUMARIC ACID(e)-p-coumaricacid
p-Hydroxyphenylacrylic acidCinnamic acid, p-hydroxy-3-(4-Hydroxyphenyl)-2-propenoic acid(E)-3-(4-Hydroxyphenyl)-2-propenoic acidbeta-(4-Hydroxyphenyl)acrylic acidCinnamic acid, p-hydroxy-, (E)-(2E)-3-(4-hydroxyphenyl)acrylic acidIBS9D1EU3J
Datenbank-Bezeichner
- CAS
501-98-4、7400-08-0- PubChem CID
- 637542
- DTXSID
DTXSID30901076- ChEMBL
CHEMBL66879- ChEBI
CHEBI:36090- UNII
- IBS9D1EU3J
- EC Number
- 231-000-0、610-511-6
- Nikkaji
- J6.196D、J8.929J
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,5
- Polarare Oberfläche (TPSA)
- 57,5 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 12
- Formalladung
- 0
- Komplexität
- 178
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
Cosmetics
Skin conditioning
Personal care product
SpringerMaterials PropertiesChemical diffusion
LogP1.79
Melting Point211.5 °C
Physical DescriptionSolid
Collision Cross Section
127 Ų [M+H-H2O]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
131.1 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
131.3 Ų [M-H]-
Physikochemische Eigenschaften
- Schmelzpunkt
- 214 °C · 214 °C (dec.)(lit.)
- Siedepunkt
- 231.61 °C · 231.61°C (rough estimate)
- Dichte
- 1.1403 · 1.1403 (rough estimate)
- Brechungsindex
- 1.45 · 1.4500 (estimate)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- Löslichkeit
- 50 mg/mL · ethanol: soluble50mg/mL
- Aggregatzustand
- Powder
- pka
- 4.65 · 4.65±0.10(Predicted)
- Farbe
- Off-white to beige or greenish
- Geruch (Odor)
- 100 % · at 100.00%. balsamic
- Wasserlöslichkeit
- soluble
- Merck
- 14 · 14,2560
- BRN
- 2207383 · 2207383
- Henry's Law Constant
- 7.2 · 7.2×105 mol/(m3Pa) at 25℃, Abraham and Jr. (2019)
- Stabilität
- Light Sensitive
- Major Application
- food and beverages
- InChI
- 1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+
- InChIKey
- NGSWKAQJJWESNS-ZZXKWVIFSA-N
- SMILES
- OC(=O)\C=C\c1ccc(O)cc1
- LogP
- 1.46 · 1.460
- CAS Datenbank
- 501 · 501-98-4(CAS DataBase Reference)
- NIST chemische Informationen
- p-Hydroxycinnamic acid(501-98-4)
- EPA chemische Informationen
- 2 · 2-Propenoic acid, 3-(4-hydroxyphenyl)-, (2E)- (501-98-4)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 75 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
H301+H311 (63.6%): Toxic if swallowed or in contact with skin [Danger Acute toxicity, oral; acute toxicity, dermal]
Gefahrenhinweise
Regulatory Information
Status: Active Update: 28-08-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/26756
4-Hydroxycinnamic acid, trans: Does not have an individual approval but may be used under an appropriate group standard
4-Hydroxycinnamic acid: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and Categories
Acute Tox. 3 (68.2%)
Skin Irrit. 2 (100%)
Sicherheitsdaten
- wgk
- 2
- hs_code
- 29163990
- RTECS-Nr.
- GD9095000
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26-36-37/39
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
Chemie und Industrie
Pharmakologische Informationen
MeSH Pharmacological Classification
Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
Chemical substances or agents with contraceptive activity in males. Use for male contraceptive agents in general or for which there is no specific heading.
Substances that eliminate free radicals. Among other effects, they protect PANCREATIC ISLETS against damage by CYTOKINES and prevent myocardial and pulmonary REPERFUSION INJURY.
Tissue LocationsFibroblasts
Cellular LocationsCytoplasm
Verwendung und Herstellung
Use ClassificationCosmetics -> Skin conditioning
General Manufacturing Information2-Propenoic acid, 3-(4-hydroxyphenyl)-: ACTIVE
Darstellung
synthetischeSynthesis of p-Coumaric acid: take o-acetylsalicyloyl chloride as raw material, in the presence of magnesium chloride, react with diethyl malonate in acetonitrile solvent, then add triethylamine, and react at 0°C for 1 h to obtain ( 2-acetoxybenzoyl) diethyl malonate product, then heated to 50°C in potassium hydroxide/methanol solution, reacted for 3h, and cyclized to obtain p-Coumaric acid.
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Ergänzende Hinweise
DefinitionChEBI: p-coumaric acid is the trans-isomer of 4-coumaric acid. 4-coumaric acid is a coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring. It has a role as a plant metabolite. It is a conjugate acid of a 4-coumarate.
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