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480-23-9

480-23-9 structure
480-23-9 structure
  • Name: Orobol
  • Chemical Name: orobol
  • CAS Number: 480-23-9
  • Molecular Formula: C15H10O6
  • Molecular Weight: 286.236
  • Catalog: Natural product Flavonoids
  • Create Date: 2018-12-10 16:01:00
  • Modify Date: 2025-08-25 18:01:05
  • 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].
Name orobol
Synonyms 3-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
4H-1-Benzopyran-4-one, 3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-
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
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
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.
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

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
Hazard Codes Xi
552-58-9 structure

552-58-9

~%

480-23-9 structure

480-23-9

Literature: Chemler, Joseph A.; Lim, Chin Giaw; Daiss, John L.; Koffas, Mattheos A.G. Chemistry and Biology, 2010 , vol. 17, # 4 p. 392 - 401
40316-84-5 structure

40316-84-5

~%

480-23-9 structure

480-23-9

Literature: Narasimhachari; Seshadri Proceedings - Indian Academy of Sciences, Section A, 1950 , # 32 p. 342,345
20486-33-3 structure

20486-33-3

~%

480-23-9 structure

480-23-9

Literature: Anhut, Siegbert; Zinsmeister, H. Dietmar; Mues, Ruediger; Barz, Wolfgang; Mackenbrock, Klaus; et al. Phytochemistry (Elsevier), 1984 , vol. 23, # 5 p. 1073 - 1076
446-72-0 structure

446-72-0

~%

480-23-9 structure

480-23-9

Literature: Roberts-Kirchhoff, Elizabeth S.; Crowley, Jan R.; Hollenberg, Paul F.; Kim, Hyesook Chemical Research in Toxicology, 1999 , vol. 12, # 7 p. 610 - 616
66026-81-1 structure

66026-81-1

~%

480-23-9 structure

480-23-9

Literature: Heerden, Fanie R. van; Brandt, E. Vincent; Roux, David G. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980 , p. 2463 - 2469
118949-94-3 structure

118949-94-3

~%

480-23-9 structure

480-23-9

Literature: Heerden, Fanie R. van; Brandt, E. Vincent; Roux, David G. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980 , p. 2463 - 2469
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