480-23-9

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: 2024-01-05 22:56:56
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	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.

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

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

480-23-9

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

20486-33-3

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

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

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

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

Precursor 4
552-58-9 446-72-0 66026-81-1 118949-94-3
DownStream 0

480-23-9	36190-95-1
66026-81-1	529-60-2
104668-88-4	101072-83-7
20486-33-3