Alpinetin - 10mM in DMSO , CAS No.36052-37-6

CAS: 36052-37-6 Cat. No.: A423623 Molecular Weight: 270.28

GRADE & PURITY 10mM in DMSO

Synonyms

(2S)-7-hydroxy-5-methoxy-2-phenyl-2,3-dihydrochromen-4-one | 4H-1-BENZOPYRAN-4-ONE, 2,3-DIHYDRO-7-HYDROXY-5-METHOXY-2-PHENYL-, (S)- | A874456 | Alpinetin,(S) | Q4735601 | (S)-7-Hydroxy-5-methoxy-2-phenylchroman-4-one | AKOS015896758 | n-Propylether | (2S)

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Alpinein (-) - apinetin) is a natural flavonoid product isolated from cardamom, which can activate PPAR - γ and has anti-inflammatory and antibacterial activities. It has strong anti hepatoma and pancreatic cancer cell effects by inhibiting proliferation, regulating the expression of Bcl-2 family and XIAP, releasing cytochrome c and activating caspase.

Specifications

Synonyms

(2S)-7-hydroxy-5-methoxy-2-phenyl-2, 3-dihydrochromen-4-one | 4H-1-BENZOPYRAN-4-ONE, 2, 3-DIHYDRO-7-HYDROXY-5-METHOXY-2-PHENYL-, (S)- | A874456 | Alpinetin, (S) | Q4735601 | (S)-7-Hydroxy-5-methoxy-2-phenylchroman-4-one | AKOS015896758 | n-Propylether | (2S)

Specifications & Purity

10mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

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

Names and Identifiers

• Canonical Smiles: COC1=CC(=CC2=C1C(=O)CC(O2)C3=CC=CC=C3)O
• IUPAC Name: (2S)-7-hydroxy-5-methoxy-2-phenyl-2,3-dihydrochromen-4-one
• InChIKey: QQQCWVDPMPFUGF-ZDUSSCGKSA-N
• INCHI: 1S/C16H14O4/c1-19-14-7-11(17)8-15-16(14)12(18)9-13(20-15)10-5-3-2-4-6-10/h2-8,13,17H,9H2,1H3/t13-/m0/s1
• Isomeric SMILES: COC1=CC(=CC2=C1C(=O)C[C@H](O2)C3=CC=CC=C3)O
• Molecular Weight: 270.28
• Reaxy-Rn: 269371
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=269371&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Flavonoids
      • Subclass O-methylated flavonoids

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Flavonoids
• Subclass: O-methylated flavonoids
• Intermediate Tree Nodes: Not available
• Direct Parent: 5-O-methylated flavonoids
• Alternative Parents: Flavanones 7-hydroxyflavonoids Chromones Aryl alkyl ketones Anisoles Alkyl aryl ethers 1-hydroxy-2-unsubstituted benzenoids Benzene and substituted derivatives Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 5-methoxyflavonoid-skeleton - 7-hydroxyflavonoid - Flavanone - Hydroxyflavonoid - Flavan - Chromone - Chromane - Benzopyran - 1-benzopyran - Anisole - Aryl ketone - Aryl alkyl ketone - Alkyl aryl ether - 1-hydroxy-2-unsubstituted benzenoid - Monocyclic benzene moiety - Benzenoid - Ketone - Organoheterocyclic compound - Oxacycle - Ether - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as 5-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C5 atom of the flavonoid backbone.
• External Descriptors: Not available

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)

FABP4 Tchem Fatty acid binding protein adipocyte (764 Activities)

Discover Target: FABP4

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

Mechanisms of Action

Chemical and Physical Properties

• Melt Point(°C): 219 °C
• Molecular Weight: 270.280 g/mol
• XLogP3: 2.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 270.089 Da
• Monoisotopic Mass: 270.089 Da
• Topological Polar Surface Area: 55.800 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 350.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Chunli Qi, Jiangnan Fu, Huinan Zhao, Huijie Xing, Dong Dong, Baojian Wu.  (2018)  Identification of UGTs and BCRP as potential pharmacokinetic determinants of the natural flavonoid alpinetin.  XENOBIOTICA,      [PMID:29436891] [10.1080/00498254.2018.1440657]

2. Mei Feng, Xinxiang Chen, Fan Huang, Lin Chen, Can Liu, Wei Li, Yinyan Li, Shaobin Chen, Zhen Deng, Zhengyi Wei, Yuan Luo, Xiyong Yu, Aiping Qin.  (2025)  Alpinetin Alleviates Cardiac Inflammation and Remodeling via TLR4/MyD88/NF-κB Signaling Pathway in Rats with Acute Myocardial Infarction.  INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES,  26  (20): (10073).  [PMID:41155364] [10.3390/ijms262010073]