| Identification | Back Directory | [Name]
6-(3-Methyl-2-butenyl)-5,7-dimethoxy-2H-1-benzopyran-2-one | [CAS]
4335-12-0 | [Synonyms]
Toddaculin
Toddaculine
5,7-dimethoxy-6-(3'-methyl-2'-butenyl)coumarin
6-(3-Methyl-2-butenyl)-5,7-dimethoxy-2H-1-benzopyran-2-one
5,7-Dimethoxy-6-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one | [Molecular Formula]
C16H18O4 | [MDL Number]
MFCD30475690 | [MOL File]
4335-12-0.mol | [Molecular Weight]
274.31 |
| Chemical Properties | Back Directory | [Melting point ]
95 °C | [Boiling point ]
432.8±45.0 °C(Predicted) | [density ]
1.138±0.06 g/cm3(Predicted) | [form ]
Solid | [color ]
White to off-white | [InChI]
InChI=1S/C16H18O4/c1-10(2)5-6-11-13(18-3)9-14-12(16(11)19-4)7-8-15(17)20-14/h5,7-9H,6H2,1-4H3 | [InChIKey]
KRQHZFHWEAJPNO-UHFFFAOYSA-N | [SMILES]
C1(=O)OC2=CC(OC)=C(C/C=C(/C)\C)C(OC)=C2C=C1 | [LogP]
4.151 (est) |
| Hazard Information | Back Directory | [Uses]
Toddaculin is a natural coumarin that can induce differentiation and apoptosis in leukemic cells. Toddaculin suppresses excess osteoclast activity and enhances osteoblast differentiation and mineralization. Toddaculin also exhibits anti-inflammatory activity[1][2][3]. | [References]
[1] Vázquez R, et, al. Toddaculin, a natural coumarin from Toddalia asiatica, induces differentiation and apoptosis in U-937 leukemic cells. Phytomedicine. 2012 Jun 15;19(8-9):737-46. DOI:10.1016/j.phymed.2012.03.008
[2] Watanabe A, et, al. Toddaculin, Isolated from of Toddalia asiatica (L.) Lam., Inhibited Osteoclastogenesis in RAW 264 Cells and Enhanced Osteoblastogenesis in MC3T3-E1 Cells. PLoS One. 2015 May 18;10(5):e0127158. DOI:10.1371/journal.pone.0127158
[3] Kumagai M, et, al. Evaluation of Aculeatin and Toddaculin Isolated from Toddalia asiatica as Anti-inflammatory Agents in LPS-Stimulated RAW264 Macrophages. Biol Pharm Bull. 2018;41(1):132-137. DOI:10.1248/bpb.b17-00607 |
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