| Identification | Back Directory | [Name]
3-(2,4-Dihydroxyphenyl)-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one | [CAS]
32884-36-9 | [Synonyms]
Cajanin
2',4',5-Trihydroxy-7-methoxyisoflavone
3-(2,4-Dihydroxyphenyl)-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one, 3-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy- | [EINECS(EC#)]
628-471-3 | [Molecular Formula]
C16H12O6 | [MOL File]
32884-36-9.mol | [Molecular Weight]
300.26 |
| Chemical Properties | Back Directory | [Melting point ]
208-210 °C(Solv: acetone (67-64-1)) | [Boiling point ]
605.5±55.0 °C(Predicted) | [density ]
1.512±0.06 g/cm3(Predicted) | [form ]
Solid | [pka]
6.19±0.20(Predicted) | [color ]
Off-white to light yellow |
| Hazard Information | Back Directory | [Uses]
Cajanin is a potent and orally active anti-melanogenic agent. Cajanin shows antiproliferative activity in MNT1 Cells. Cajanin efficiently decreases the melanin content. Cajanin down-regulates the mRNA and protein expression levels of MITF, tyrosinase, TRP-1 and Dct (TRP-2). Cajanin induces cell cycle arrest at G2/M and S phase. Cajanin stimulates osteoblast proliferation. Cajanin has the potential for the research of human hyperpigmented disorders and menopausal osteoporosis[1][2]. | [Definition]
ChEBI: Cajanin is a member of 7-methoxyisoflavones. It has a role as a metabolite. | [in vivo]
Cajanin (10 mg/kg, p.o.; daily for 30 consecutive days) increases the BMD levels in all anatomical regions of the skeleton studied in Sprague Dawley rats[1]. | [References]
[1] Netcharoensirisuk P, et al. Cajanin Suppresses Melanin Synthesis through Modulating MITF in Human Melanin-Producing Cells. Molecules. 2021 Oct 5;26(19):6040. DOI:10.3390/molecules26196040
[2] Bhargavan B, et al. Methoxylated isoflavones, cajanin and isoformononetin, have non-estrogenic bone forming effect via differential mitogen activated protein kinase (MAPK) signaling. J Cell Biochem. 2009 Oct 1;108(2):388-99. DOI:10.1002/jcb.22264
[3] Wensaas AJ, et al. Fatty acid incubation of myotubes from humans with type 2 diabetes leads to enhanced release of beta-oxidation products because of impaired fatty acid oxidation: effects of tetradecylthioacetic acid and eicosapentaenoic acid. Diabetes. 2009 Mar;58(3):527-35. DOI:10.2337/db08-1043 |
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