Bavachalcone - ≥98% , CAS No.28448-85-3

CAS: 28448-85-3 Cat. No.: B709870 Molecular Weight: 324.37

GRADE & PURITY ≥98%

Synonyms

Bavachalcone | broussochalcone B | (E)-1-[2,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one | (E)-1-(2,4-Dihydroxy-5-(3-methyl-but-2-enyl)-phenyl)-3-(4-hydroxy-phenyl)-propenone | (E)-1-[2,4-Dihydroxy-5-(3-methyl-but-2-enyl)-p

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Bavachalcone is a potent inducer of apoptosis. Bavachalcone exerts anticancer activity by promoting autophagy and apoptosis in HepG2 cells. Bavachalcone acts as an anti-neuroinflammatory and antidepressant through the NF-κB pathway. Bavachalcone inhibits osteoclasts by interfering with ERK and Akt signaling pathways and the expression of c-Fos and NFATc1. Bavachalcone exhibits a significant inhibitory effect on baculovirus-expressed BACE-1 in vitro.

Specifications

Synonyms

Bavachalcone | broussochalcone B | (E)-1-[2, 4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one | (E)-1-(2, 4-Dihydroxy-5-(3-methyl-but-2-enyl)-phenyl)-3-(4-hydroxy-phenyl)-propenone | (E)-1-[2, 4-Dihydroxy-5-(3-methyl-but-2-enyl)-p

Specifications & Purity

≥98%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

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

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC(=CCC1=CC(=C(C=C1O)O)C(=O)C=CC2=CC=C(C=C2)O)C
• IUPAC Name: (E)-1-[2,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
• InChIKey: BLZGPHNVMRXDCB-UXBLZVDNSA-N
• INCHI: 1S/C20H20O4/c1-13(2)3-7-15-11-17(20(24)12-19(15)23)18(22)10-6-14-4-8-16(21)9-5-14/h3-6,8-12,21,23-24H,7H2,1-2H3/b10-6+
• Isomeric SMILES: CC(=CCC1=CC(=C(C=C1O)O)C(=O)/C=C/C2=CC=C(C=C2)O)C
• Alternate CAS: 28448-85-3
• MeSH Entry Terms: bavachalcone
• Molecular Weight: 324.37

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Linear 1,3-diarylpropanoids
      • Subclass Chalcones and dihydrochalcones

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Linear 1,3-diarylpropanoids
• Subclass: Chalcones and dihydrochalcones
• Intermediate Tree Nodes: Not available
• Direct Parent: 3-prenylated chalcones
• Alternative Parents: 2'-Hydroxychalcones Cinnamylphenols Hydroxycinnamic acids and derivatives Styrenes Resorcinols Benzoyl derivatives Aryl ketones 1-hydroxy-2-unsubstituted benzenoids Vinylogous acids Enones Acryloyl compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: 3-prenylated chalcone - 2'-hydroxychalcone - Cinnamylphenol - Hydroxycinnamic acid or derivatives - Benzoyl - Aryl ketone - Resorcinol - Styrene - Phenol - 1-hydroxy-2-unsubstituted benzenoid - Monocyclic benzene moiety - Benzenoid - Vinylogous acid - Alpha,beta-unsaturated ketone - Enone - Acryloyl-group - Ketone - Hydrocarbon derivative - Organooxygen compound - Organic oxide - Organic oxygen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position.
• External Descriptors: Chalcones and dihydrochalcones

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)

CYP19A1 Tclin Cytochrome P450 19A1 (6099 Activities)

Discover Target: CYP19A1

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K562 (73714 Activities)

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A549 (127892 Activities)

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HUVEC (11049 Activities)

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SIRT1 Tchem NAD-dependent deacetylase sirtuin 1 (3505 Activities)

Discover Target: SIRT1

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Associated Targets(non-human)

MAL62 Alpha-glucosidase MAL62 (106 Activities)

Discover Target: MAL62

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Micrococcus luteus (7463 Activities)

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Staphylococcus epidermidis (22802 Activities)

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Bacillus subtilis (32866 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 324.400 g/mol
• XLogP3: 5.100
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 324.136 Da
• Monoisotopic Mass: 324.136 Da
• Topological Polar Surface Area: 77.800 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 470.000
• 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. Shuai Shi, Xiaohan Bian, Mengyun Li, Xiaobing Zhang, Wenji Huang, Xian Shao, Tiantian Lu, Xuebin Yu.  (2025)  Neuroprotective effects of bavachalcone in a mouse model of Parkinson’s disease: linking the gut-brain axis and systemic metabolism.  Frontiers in Neuroscience,      [PMID:41059096] [10.3389/fnins.2025.1650288]