| Identification | Back Directory | [Name]
LOUREIRIN B | [CAS]
119425-90-0 | [Synonyms]
LOUREIRIN B
cochinchinenin B
LOUREIRIN B USP/EP/BP
1-Propanone,1-(4-hydroxyphenyl)-3-(2,4,6-triMethoxyphenyl)
1-(4-hydroxyphenyl)-3-(2,4,6-trimethoxyphenyl)propan-1-one
Loureirin B, 98%, from Dracaena cochinchinensis (Lour.) S. C. Chen | [Molecular Formula]
C18H20O5 | [MDL Number]
MFCD07781421 | [MOL File]
119425-90-0.mol | [Molecular Weight]
316.35 |
| Chemical Properties | Back Directory | [Boiling point ]
509.9±50.0 °C(Predicted) | [density ]
1.177±0.06 g/cm3(Predicted) | [solubility ]
DMF: 30 mg/ml; DMSO: 30 mg/ml; DMSO:PBS (pH 7.2) (1:2): 0.33 mg/ml | [form ]
powder | [pka]
8.06±0.15(Predicted) | [color ]
White | [InChI]
1S/C18H20O5/c1-21-14-10-17(22-2)15(18(11-14)23-3)8-9-16(20)12-4-6-13(19)7-5-12/h4-7,10-11,19H,8-9H2,1-3H3 | [InChIKey]
ZPFRAPVRYLGYEC-UHFFFAOYSA-N | [SMILES]
O(C)c1c(c(cc(c1)OC)OC)CCC(=O)c2ccc(cc2)O |
| Hazard Information | Back Directory | [Chemical Properties]
White powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from the resin of the Dracaena frondosa tree. | [Uses]
Loureirin B is a component of traditional Chinese medicine which helps combat neurodegenerative diseases. Extracted from the red resin of Dracaena cochinchinensis S.C Chen, known as Dragon’s Blood. | [Synthesis]
After benzyl protection, 4-hydroxyacetophenone undergoes condensation with 2,4,6-trimethoxybenzaldehyde under strong base catalysis (such as sodium hydroxide) to generate the corresponding chalcone intermediate. Finally, hydrogenation is carried out at atmospheric pressure using palladium on carbon (Pd/C) as a catalyst to remove the benzyl protecting group and simultaneously reduce the chalcone double bond, yielding Loureirin B. | [in vivo]
Loureirin B significantly improves the arrangement and deposition of collagen fibres, decreases protein levels of ColI, ColIII and α-SMA and suppresses myofibroblast differentiation and scar proliferative activity, in a rabbit ear scar model. Loureirin B effectively inhibits TGF-β1-induced upregulation of ColI, ColIII and α-SMA levels, myofibroblast differentiation and the activation of Smad2 and Smad3, in NS fibroblasts[3]. | [IC 50]
PAI-1: 26.1 μM (IC50); KATP; ERK; JNK |
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