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435800

Sigma-Aldrich

Licochalcone-A, Synthetic

≥96% (HPLC), estrogenic flavonoid, solid

Synonym(s):

Licochalcone-A, Synthetic, (E)-3-[5-(1,1-Dimethyl-2-propenyl)-4-hydroxy-2-methoxyphenyl]-1-(4-hydroxyphenyl)-2-propen-1-one

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About This Item

Empirical Formula (Hill Notation):
C21H22O4
CAS Number:
58749-22-7
Molecular Weight:
338.40
MDL number:
MFCD01417903
UNSPSC Code:
12352200
NACRES:
NA.77

Product Name

Licochalcone-A, Synthetic, An estrogenic flavonoid with anti-tumor and antiparasitic properties.

Quality Level

100

Assay

≥96% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

yellow

solubility

DMSO: 10 mg/mL
ethanol: soluble

shipped in

ambient

storage temp.

−20°C

SMILES string

O(C)c1c(cc(c(c1)O)C(C)(C)C=C)\C=C\C(=O)c2ccc(cc2)O

InChI

1S/C21H22O4/c1-5-21(2,3)17-12-15(20(25-4)13-19(17)24)8-11-18(23)14-6-9-16(22)10-7-14/h5-13,22,24H,1H2,2-4H3/b11-8+

InChI key

KAZSKMJFUPEHHW-DHZHZOJOSA-N

General description

An estrogenic flavanoid with anti-tumor and anti-parasitic properties. Shown to reduce Bcl-2 protein expression and induce apoptosis in several human cancer cell lines. Also induces cell differentiation and enhances the effect of paclitaxel and vinblastine chemotherapy. Reported to interfere with parasite mitochondrial electron transport chain and energy metabolism.
An estrogenic flavonoid with anti-tumor and antiparasitic properties. Shown to reduce Bcl-2 protein expression and induce apoptosis in several human cancer cell lines. Also induces cell differentiation, exhibits anti-tumor activity, and enhances the effect of Paclitaxel (Cat. No. 580555) and Vinblastine (Cat. No. 677175) chemotherapy. Reported to interfere with parasite mitochondrial electron transport chain and energy metabolism.

Biochem/physiol Actions

Cell permeable: no
Primary Target
Anti-tumor and antiparasitic properties
Product does not compete with ATP.
Reversible: no

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution aliquot and freeze at -20°C. Stock solutions are stable for up to 6 months at -20°C.
Further dilute 1:10 with aqueous buffer or medium just prior to use.

Other Notes

Rafi, M.M., et al. 2000. Anticancer Res. 20, 2653.
Zhai, L., et al. 1999. J. Antimicrob. Chemother. 43, 793.
Haraguchi, H., et al. 1998. Phytochemistry 48, 125.
Park, E.J., et al. 1998. Planta Med. 64, 464.
Chen, M., et al. 1994. Antimicrob. Agents Chemother. 38, 1470.
Chen, M., et al. 1993. Antimicrob. Agents. Chemother. 37, 2550.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Harmful (C)

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 + H312 + H332

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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