ChemicalBook > CAS DataBase List > ISOBAVACHALCONE

ISOBAVACHALCONE

Product Name: ISOBAVACHALCONE
CAS No.: 20784-50-3
Chemical Name: ISOBAVACHALCONE
Synonyms: CS-446;ISOBAVACHALCONE;Isobacachalcone;Isobawachalcone;Isobavachalcone-RM;Isobavachalcone/Corylifolinin;Corylifolinin(Isobavachalcone);Isobavachalcone, Akt inhibitor;Isobavachalcone, 10 mM in DMSO;(E)-4,2',4'-Trihydroxy-3'-prenylchalcone
CBNumber: CB91412753
Molecular Formula: C20H20O4
Formula Weight: 324.37
MOL File: 20784-50-3.mol

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ISOBAVACHALCONE Property

Melting point:: 156.8-157.8 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
Boiling point:: 549.0±50.0 °C(Predicted)
Density: 1.243±0.06 g/cm3(Predicted)
storage temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility: Soluble in DMSO
pka: 7.99±0.40(Predicted)
form: Yellow oil.
color: Yellow-orange
InChI: InChI=1S/C20H20O4/c1-13(2)3-9-16-19(23)12-10-17(20(16)24)18(22)11-6-14-4-7-15(21)8-5-14/h3-8,10-12,21,23-24H,9H2,1-2H3/b11-6+
InChIKey: DUWPGRAKHMEPCM-IZZDOVSWSA-N
SMILES: C(C1=CC=C(O)C(C/C=C(/C)\C)=C1O)(=O)/C=C/C1=CC=C(O)C=C1

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML1450
Product name: Isobavachalcone
Purity: ≥98% (HPCE)
Packaging: 5mg
Price: $118
Updated: 2025/07/31

Sigma-Aldrich

Product number: SML1450
Product name: Isobavachalcone
Purity: ≥98% (HPCE)
Packaging: 25mg
Price: $462
Updated: 2025/07/31

Sigma-Aldrich

Product number: PHL83317
Product name: Isobavachalcone
Purity: phyproof? Reference Substance
Packaging: 10mg
Price: $448
Updated: 2025/07/31

TCI Chemical

Product number: I1232
Product name: Isobavachalcone
Packaging: 100MG
Price: $345
Updated: 2025/07/31

Cayman Chemical

Product number: 19873
Product name: Isobavachalcone
Purity: ≥98%
Packaging: 5mg
Price: $81
Updated: 2024/03/01

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ISOBAVACHALCONE Chemical Properties,Usage,Production

Chemical Properties

Yellow crystalline powder, soluble in organic solvents such as methanol, ethanol, DMSO, etc., derived from Psoralea corylifolia Linn.

Uses

Isobavachalcone is an inhibitor of platelet aggregation.

Definition

ChEBI: A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4' and a prenyl group at position 3'.

Biological Activity

Isobavachalcone is a chalcone isolated from multipurpose medical plant Psoralea corylifolia th at inhibits LPS-induced ICAM-1 expression and leukocyte adhesion to brain endothelial cells. It appears th at isobavachalcone modulates both MyD88-dependent and TRIF-dependent signaling of toll-like receptor 4 (TLR4). Isobavachalcone significantly inhibits both oligomerization and fibrillization of Aβ42. Isobavachalcone exhibits a wide spectrum of biological activities including antioxidative, antiplatelet, antimicrobial, anti-inflammatory, antitumor, and neuroprotective.

Synthesis

1449202-18-9

54676-49-2

The general procedure for the synthesis of 1-(2,4-dihydroxy-3-(3-methyl-2-buten-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one from the compound (CAS: 1449202-18-9) is as follows: General method: 1. Compound 13 (100 mg, 0.22 mmol) was dissolved in methanol (2 mL) at 0 °C and 1N aqueous hydrochloric acid solution (1 mL) was slowly added. 2. The reaction mixture was heated to 50 °C and maintained at this temperature for 6 hours. 3. Upon completion of the reaction, the mixture was cooled to room temperature and the methanol was subsequently removed under vacuum. 4. The organic and aqueous layers were separated by adding ethyl acetate (10 mL) for extraction. 5. The aqueous layer was further extracted with ethyl acetate (2 x 10 mL) and all organic layers were combined. 6. The organic layer was dried with anhydrous magnesium sulfate, filtered and concentrated in vacuum to obtain the crude product. 7. The crude product was purified by rapid chromatography on silica gel, the eluent was n-hexane/ethyl acetate (15:1), and the target product, bavarone (53 mg, yield 75%), was obtained as a yellow solid. Note: This method is also applicable to the preparation of Compound 1 using Compound 22 (100 mg, 0.22 mmol) as substrate under the same reaction conditions as above, resulting in Compound 1 (53 mg, 75% yield) as a yellow solid.

in vivo

Isobavachalcone (20 mg/kg; intraperitoneal injection; for 0.5-24 hours; female Kunming mice) treatment results in an increase in blood glucose levels, reaching a maximum within 1 hour and maintaining until 4 hours post-dosing^[1].

Animal Model:	Seven-week-old specific pathogen-free female Kunming mice (18-22 g)^[1]
Dosage:	20 mg/kg
Administration:	Intraperitoneal injection; for 0.5, 1, 2, 4, 6, 8, 12, 24 hours
Result:	Increased in blood glucose levels.

References

[1] Tetrahedron Letters, 2014, vol. 55, # 4, p. 897 - 899
[2] Tetrahedron Letters, 2014, vol. 55, # 4, p. 897 - 899
[3] European Journal of Medicinal Chemistry, 2015, vol. 92, p. 439 - 448

ISOBAVACHALCONE Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from ISOBAVACHALCONE manufacturers

Shanghai Standard Technology Co., Ltd.

Product: Isobavachalcone 20784-50-3
Price: US $0.00/mg
Min. Order: 5mg
Purity: ≥98%(HPLC)
Supply Ability: 10 g
Release date: 2019-11-11

Career Henan Chemical Co

Product: ISOBAVACHALCONE 20784-50-3
Price: US $1.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 25kg
Release date: 2019-07-12

20784-50-3, ISOBAVACHALCONERelated Search:

ISOEGOMAKETONE Tenuifoliside C Notoginseng triterpenes NARINGIN HYDRATE TECH. DRACORHODIN PEROCHLORATE Pinostrobin 3-ACETYL-11-KETO-BETA-BOSWELLIC ACID kaurenoic acid Epmedin C Epmedin B Epimedin A trans-Chalcone Icariin EPIMEDIOSIDE 2'-O-RHAMNOSYLICARISIDE II ISOBAVACHALCONE Xanthohumol DESMETHYLXANTHOHUMOL

ISOBAVACHALCONE

(E)-1-[2,4-Dihydroxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one

(E)-4,2',4'-Trihydroxy-3'-prenylchalcone

2',4,4'-Trihydroxy-3'-prenyl-trans-chalcone

Isobacachalcone

2-Propen-1-one,1-[2,4-dihydroxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-, (2E)-

(2E)-1-[2,4-Dihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one

CS-446

Corylifolinin(Isobavachalcone)

Isobavachalcone/Corylifolinin

2-Propen-1-one, 1-[2,4-dihydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-, (2E)-

(E)-1-(2,4-Dihydroxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

(E)-1-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one

(2E)-1-[2,4-Dihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-...

Isobawachalcone

Isobavachalcone-RM

Isobavachalcone, Akt inhibitor

Isobavachalcone, 10 mM in DMSO

20784-50-3

PI3K/Akt/mTOR

Akt

mTOR

PI3K