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4335-12-0

4335-12-0 Structure

4335-12-0 Structure
IdentificationBack 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 PropertiesBack 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 InformationBack 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
Spectrum DetailBack Directory
[Spectrum Detail]

6-(3-Methyl-2-butenyl)-5,7-dimethoxy-2H-1-benzopyran-2-one(4335-12-0)1HNMR
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