trans-3,5-Dimethoxy-4-hydroxycinnamaldehyde - Moligand™, ≥98% , CAS No.4206-58-0

CAS: 4206-58-0 Cat. No.: I170272 Formula: HOC₆H₂(OCH₃)₂CH=CHCHO Molecular Weight: 208.21 EC Number: 627-731-3

GRADE & PURITY Moligand™, ≥98%

Synonyms

bmse010085 | Sinapinaldehyde | ACon1_001103 | MFCD00075980 | 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enal | SCHEMBL197270 | 3,4-dimethoxy-4-hydroxycinnamaldehyde | AKOS015999009 | 2-Propenal, 3-(4-hydroxy-3,5-dimethoxyphenyl)-, (2E)- | (E)-sinapoyl aldehy

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

Sinapaldehyde is a methoxyphenol and a selective COX-2 inhibitor (IC50: 47.8 µM) that can be extracted from various plants. Sinapaldehyde has antibacterial, anti-inflammatory, and antioxidant activities. Sinapaldehyde can scavenge DPPH free radicals (IC50: 172 μM). Sinapaldehyde is active against both Gram-negative and Gram-positive bacteria.

Specifications

Synonyms

bmse010085 | Sinapinaldehyde | ACon1_001103 | MFCD00075980 | 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enal | SCHEMBL197270 | 3,4-dimethoxy-4-hydroxycinnamaldehyde | AKOS015999009 | 2-Propenal, 3-(4-hydroxy-3,5-dimethoxyphenyl)-, (2E)- | (E)-sinapoyl aldehy

Specifications & Purity

Moligand™, ≥98%

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

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

Grade

Moligand™

Action Type

INHIBITOR

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504763313
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763313
• Canonical Smiles: COC1=CC(=CC(=C1O)OC)C=CC=O
• IUPAC Name: (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enal
• InChIKey: CDICDSOGTRCHMG-ONEGZZNKSA-N
• INCHI: 1S/C11H12O4/c1-14-9-6-8(4-3-5-12)7-10(15-2)11(9)13/h3-7,13H,1-2H3/b4-3+
• Isomeric SMILES: COC1=CC(=CC(=C1O)OC)/C=C/C=O
• WGK Germany: 3
• Molecular Weight: 208.21
• Reaxy-Rn: 2215798
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2215798&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Phenols
      • Subclass Methoxyphenols

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Phenols
• Subclass: Methoxyphenols
• Intermediate Tree Nodes: Not available
• Direct Parent: Methoxyphenols
• Alternative Parents: Dimethoxybenzenes Cinnamaldehydes Styrenes Phenoxy compounds Anisoles Alkyl aryl ethers Enals Organic oxides Hydrocarbon derivatives Aldehydes
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Cinnamaldehyde - Methoxyphenol - Dimethoxybenzene - M-dimethoxybenzene - Methoxybenzene - Anisole - Phenoxy compound - Styrene - Phenol ether - Alkyl aryl ether - Monocyclic benzene moiety - Alpha,beta-unsaturated aldehyde - Enal - Ether - Aldehyde - Carbonyl group - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as methoxyphenols. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
• External Descriptors: Sinapate derivatives

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(Human)

LoVo (4724 Activities)

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PC-3 (62116 Activities)

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SK-MEL-28 (48833 Activities)

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Associated Targets(non-human)

L1210 (27553 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Melt Point(°C): 104-106 °C
• Molecular Weight: 208.210 g/mol
• XLogP3: 1.400
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 208.074 Da
• Monoisotopic Mass: 208.074 Da
• Topological Polar Surface Area: 55.800 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 213.000
• 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