Isoliquiritigenin
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Isoliquiritigenin
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CAS No:
961-29-5
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Formula:
C15H12O4
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Chemical Name:
Isoliquiritigenin
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Synonyms:
2-Propen-1-one,1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-,(2E)-;Chalcone,2′,4,4′-trihydroxy-;2-Propen-1-one,1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-,(E)-;(2E)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one;Isoliquiritigenin;2′,4,4′-Trihydroxychalcone;GU 17;Isoliquiritigen;(E)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one;78918-29-3
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CAS No:
Description
Isoliquiritigenin is an anti-tumor flavonoid from the root of Glycyrrhiza glabra, which inhibits aldose reductase with an IC50 of 320 nM.
Solid
Isoliquiritigenin is a member of the class of chalcones that is trans-chalcone hydroxylated at C-2', -4 and -4'. It has a role as an EC 1.14.18.1 (tyrosinase) inhibitor, a biological pigment, a NMDA receptor antagonist, a GABA modulator, a metabolite, an antineoplastic agent and a geroprotector. It derives from a trans-chalcone. It is a conjugate acid of an isoliquiritigenin(1-).|Isoliquiritigenin is a precursor to several flavonones in many plants.
Characteristics
77.8
3.2
yellow to orange powder
1.4±0.1 g/cm3
200 °C
504ºC at 760 mmHg
272.7±24.4 °C
1.715
H2O: <0.1 mg/mL
2-8°C
165.05 Ų [M+H]+ [CCS Type: DT, Method: stepped-field]|187.37 Ų [M+Na]+ [CCS Type: DT, Method: stepped-field]|164.24 Ų [M-H]- [CCS Type: DT, Method: stepped-field]|158.3 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|163.7 Ų [M-H]-
Safety Information
NONH for all modes of transport
3
36/37/38
26-37
FL7080000
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 5 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Drug Information
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)
2',4',4-trihydroxychalcone
Isoliquiritigenin Use and Manufacturing
Isoliquiritigenin (ISL) is a flavonoid found in licorice root and several other plants that displays antioxidant, anti-inflammatory, and antitumor activities as well as hepatoprotection against steatosis-induced oxidative stress. ISL induces quinone reduc
Polyketides [PK] -> Flavonoids [PK12] -> Chalcones and dihydrochalcones [PK1212]
Computed Properties
Molecular Weight:256.25
XLogP3:3.2
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:256.07355886
Monoisotopic Mass:256.07355886
Topological Polar Surface Area:77.8
Heavy Atom Count:19
Complexity:331
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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