cis-4-Hydroxycinnamic acid - Moligand™, ≥97% , CAS No.4501-31-9

CAS: 4501-31-9 Cat. No.: C347483 Formula: C₉H₈O₃ Molecular Weight: 164.16

GRADE & PURITY Moligand™, ≥97%

Synonyms

NSC 90284 | cis-p-Coumaric acid | EINECS 224-813-7 | (Z)-3-(4-hydroxyphenyl)acrylic acid | Q27102404 | SCHEMBL434720 | (Z)-p-Coumaric acid | cis-4-Hydroxycinnamic acid | cis-p-Coumarate | cis-p-Hydroxycinnamic acid | (2Z)-3-(4-hydroxyphenyl)prop-2-enoic a

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

cis-p-Coumaric acid (cis-4-Hydroxycinnamic acid) is the cis-form of p-Coumaric acid, which is higher in viable seeds of groundnuts than in non-viable ones. p-Coumaric acid is an isomer of cinnamic acid with oral activity. p-Coumaric acid inhibits cell proliferation and promotes Apoptosis.

Specifications

Synonyms

NSC 90284 | cis-p-Coumaric acid | EINECS 224-813-7 | (Z)-3-(4-hydroxyphenyl)acrylic acid | Q27102404 | SCHEMBL434720 | (Z)-p-Coumaric acid | cis-4-Hydroxycinnamic acid | cis-p-Coumarate | cis-p-Hydroxycinnamic acid | (2Z)-3-(4-hydroxyphenyl)prop-2-enoic a

Specifications & Purity

Moligand™, ≥97%

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Purity

≥97%

Names and Identifiers

• Canonical Smiles: C1=CC(=CC=C1C=CC(=O)O)O
• IUPAC Name: (Z)-3-(4-hydroxyphenyl)prop-2-enoic acid
• InChIKey: NGSWKAQJJWESNS-UTCJRWHESA-N
• INCHI: 1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3-
• Isomeric SMILES: C1=CC(=CC=C1/C=C\C(=O)O)O
• Molecular Weight: 164.16
• Reaxy-Rn: 2207381
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2207381&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Cinnamic acids and derivatives
      • Subclass Hydroxycinnamic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Cinnamic acids and derivatives
• Subclass: Hydroxycinnamic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Hydroxycinnamic acids
• Alternative Parents: Coumaric acids Cinnamic acids Styrenes 1-hydroxy-2-unsubstituted benzenoids Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Cinnamic acid - Coumaric acid - Coumaric acid or derivatives - Hydroxycinnamic acid - Styrene - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Monocyclic benzene moiety - Benzenoid - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Organic oxide - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as hydroxycinnamic acids. These are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
• External Descriptors: 4-coumaric acid

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(non-human)

HT-22 (3261 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Light sensitive
• Melt Point(°C): 131-133° C
• Molecular Weight: 164.160 g/mol
• XLogP3: 1.500
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 164.047 Da
• Monoisotopic Mass: 164.047 Da
• Topological Polar Surface Area: 57.500 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 178.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Huijuan Li, Xinghui Song, Huiru Li, Lifei Zhu, Shengbo Cao, Jifeng Liu.  (2022)  Sesquiterpenes and Monoterpenes from the Leaves and Stems of Illicium simonsii and Their Antibacterial Activity.  MOLECULES,  27  (3): (1115).  [PMID:35164380] [10.3390/molecules27031115]