Orobol

Names

[ CAS No. ]:
480-23-9

[ Name ]:
Orobol

[Synonym ]:
3-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
5,7,3',4'-Tetrahydroxyisoflavone
3'-hydroxygenistein
Orobol
Norsantal
3',4',5,7-tetrahydroxyisoflavone
Santol
3-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
Isoluteolin

Biological Activity

[Description]:

Orobol is one of the major soy isoflavones and has various pharmacological activities, including anti-skin-aging and anti-obesity effects. Orobol inhibits CK1ε, VEGFR2, MAP4K5, MNK1, MUSK, TOPK, and TNIK (IC50=1.24-4.45 μM). Orobol also inhibits PI3K isoforms (IC50=3.46-5.27 μM for PI3K α/β/γ/K/δ)[1][2].

[Related Catalog]:

Signaling Pathways >> PI3K/Akt/mTOR >> PI3K

Research Areas >> Metabolic Disease

Signaling Pathways >> Cell Cycle/DNA Damage >> Casein Kinase

Signaling Pathways >> Stem Cell/Wnt >> Casein Kinase

[In Vitro]

Orobol binds to CK1ε in an ATP-competitive manner and exerts anti-obesity effects by targeting casein kinase 1 epsilon[2]. Orobol (5-20 μM) effectively suppresses MDI (isobutylmethylxanthine, dexamethasone and insulin (MDI))-induced phosphorylation of 4E-BP1[2].

[In Vivo]

Orobol attenuates high fat diet-induced weight gain and lipid accumulation without affecting food intake in C57BL/6J mice[2]. Animal Model: HFD-induced obesity in C57BL/6J mice[2] Dosage: 10 mg/kg Administration: Intragastrically; daily for 23 weeks Result: Significantly reduced body weight by 17.3% compared to the HFD group.

[References]

[1]. Kim MH, et al. Lipid Nanoparticles for Enhancing the Physicochemical Stability and Topical Skin Delivery of Orobol. Pharmaceutics. 2020;12(9):845. Published 2020 Sep 3.

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Boiling Point ]:
616.1±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₅H₁₀O₆

[ Molecular Weight ]:
286.236

[ Flash Point ]:
239.5±25.0 °C

[ Exact Mass ]:
286.047729

[ PSA ]:
111.13000

[ LogP ]:
2.76

[ Vapour Pressure ]:
0.0±1.8 mmHg at 25°C

[ Index of Refraction ]:
1.768

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DJ2982400

CHEMICAL NAME :: 4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(3,4-dihydroxyphenyl)-

CAS REGISTRY NUMBER :: 480-23-9

BEILSTEIN REFERENCE NO. :: 0292790

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C15-H10-O6

MOLECULAR WEIGHT :: 286.25

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >250 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 28,947,1975

Safety Information

[ Hazard Codes ]:
Xi

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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