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Merck

68783

Licochalcone A

≥96.0% (HPLC)

Synonym(s):

(E)-3-[5-(1,1-Dimethyl-2-propenyl)-4-hydroxy-2-methoxyphenyl]-1-(4-hydroxyphenyl)-2-propen-1-one, 4′,4-Dihydroxy-3-α,α-dimethylallyl-6-methoxychalcone

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About This Item

Empirical Formula (Hill Notation):
C21H22O4
CAS Number:
58749-22-7
Molecular Weight:
338.40
UNSPSC Code:
41116107
NACRES:
NA.77
PubChem Substance ID:
329761160
MDL number:
MFCD01417903
Beilstein/REAXYS Number:
4534154

Key Documents

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Product Name

Licochalcone A, ≥96.0% (HPLC)

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+

SMILES string

COc1cc(O)c(cc1\C=C\C(=O)c2ccc(O)cc2)C(C)(C)C=C

InChI key

KAZSKMJFUPEHHW-DHZHZOJOSA-N

assay

≥96.0% (HPLC)

form

powder

storage temp.

−20°C

Quality Level

100

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This Item
PHL80486SMB01082SMB01050
Licochalcone A ≥96.0% (HPLC)

Sigma-Aldrich

68783

Licochalcone A

Licochalcone A phyproof® Reference Substance

PHL80486

Licochalcone A

Licochalcone C ≥90% (LC/MS-ELSD)

Sigma-Aldrich

SMB01082

Licochalcone C

Licochalcone B ≥85% (LC/MS-ELSD)

Sigma-Aldrich

SMB01050

Licochalcone B

assay

≥96.0% (HPLC)

assay

≥95.0% (HPLC)

assay

≥90% (LC/MS-ELSD)

assay

≥85% (LC/MS-ELSD)

form

powder

form

-

form

solid

form

solid

Quality Level

100

Quality Level

-

Quality Level

-

Quality Level

-

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

Biochem/physiol Actions

Inhibits vegetative growth of spore-forming bacteria, B. subtilis and other food-contaminating microorganisms.

General description

Licochalcone A is a potent membrane-active agent that transforms normal erythrocytes into echinocytes.[1] A novel flavanoid which has demonstrated significant antitumor activity.[2]

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM7374
BCCM7372
BCCK9487
BCCK9285
BCCK6639

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Ryo-Ichi Tsukiyama et al.
Antimicrobial agents and chemotherapy, 46(5), 1226-1230 (2002-04-18)
Licochalcone A was isolated from the roots of licorice, Glycyrrhiza inflata, which has various uses in the food and pharmaceutical industries; isolation was followed by extraction with ethanol and column chromatography with silica gel. In this study, the activities of
Ewelina Szliszka et al.
International journal of molecular sciences, 11(1), 1-13 (2010-02-18)
Chalcones exhibit chemopreventive and antitumor effects. Tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) is a naturally occurring anticancer agent that induces apoptosis in cancer cells and is not toxic to normal cells. We examined the cytotoxic and apoptotic effect of five
M Udompataikul et al.
Journal of the European Academy of Dermatology and Venereology : JEADV, 25(6), 660-665 (2010-09-16)
Although moisturizer usage has been considered a mainstay of treatment for atopic dermatitis (AD) patients, few clinical studies have been investigated. Recently, moisturizers containing non-steroidal anti-inflammatory agents, such as licochalcone A (LA) and vitamin B(12) are of emerging interest. To
Xiu-ying Xiao et al.
Cancer letters, 302(1), 69-75 (2011-01-11)
The aim of this study was to determine the anticancer effects of seven licorice compounds in MKN-28, AGS, and MKN-45 gastric cancer cells and human gastric epithelium immortalized cells. We also explored the mechanism of action of licochalcone A (LCA)
Jin-Kyung Kim et al.
Journal of molecular medicine (Berlin, Germany), 88(8), 829-838 (2010-04-13)
Licochalcone A (LicA), a major phenolic constituent of licorice, has antiproliferative and anti-inflammatory properties in human and murine cell lines. We previously showed that LicA down-regulates the expression of cyclooxygenase (COX)-2 and inducible nitric oxide synthase (iNOS) via the modulation
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