Propan-1-one, 1-(4-hydroxyphenyl)-3-(2,4,6-trimethoxyphenyl)-
LOUREIRIN B
CAS: 119425-90-0
Molecular Formula: C18H20O5
Propan-1-one, 1-(4-hydroxyphenyl)-3-(2,4,6-trimethoxyphenyl)- - Names and Identifiers
| Name | LOUREIRIN B |
| Synonyms | LR-B ColouringB LOUREIRIN B Loureirin B cochinchinenin B 1-(4-Hydroxyphenyl)-3-(2,4,6-trimethoxyphenyl)propan-1-one 1-Propanone,1-(4-hydroxyphenyl)-3-(2,4,6-triMethoxyphenyl) 1-(4-hydroxyphenyl)-3-(2,4,6-trimethoxyphenyl)propan-1-one Propan-1-one, 1-(4-hydroxyphenyl)-3-(2,4,6-trimethoxyphenyl)- |
| CAS | 119425-90-0 |
| InChI | InChI=1/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 |
Propan-1-one, 1-(4-hydroxyphenyl)-3-(2,4,6-trimethoxyphenyl)- - Physico-chemical Properties
| Molecular Formula | C18H20O5 |
| Molar Mass | 316.35 |
| Density | 1.177±0.06 g/cm3(Predicted) |
| Melting Point | 132-133°C |
| Boling Point | 509.9±50.0 °C(Predicted) |
| Flash Point | 184°C |
| Solubility | DMSO : ≥ 150 mg/mL (474.16 mM) |
| Vapor Presure | 5.12E-11mmHg at 25°C |
| Appearance | White crystal |
| pKa | 8.06±0.15(Predicted) |
| Storage Condition | 2-8℃ |
| Refractive Index | 1.563 |
| Physical and Chemical Properties | White powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from dragon blood tree resin. |
Propan-1-one, 1-(4-hydroxyphenyl)-3-(2,4,6-trimethoxyphenyl)- - Risk and Safety
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| HS Code | 29145090 |
Propan-1-one, 1-(4-hydroxyphenyl)-3-(2,4,6-trimethoxyphenyl)- - Reference
| Reference Show more | 1. [IF=5.923] Yujuan Li et al."Dragon’s Blood Regulates Rac1-WAVE2-Arp2/3 Signaling Pathway to Protect Rat Intestinal Epithelial Barrier Dysfunction Induced by Simulated Microgravity."Int J Mol Sci. 2021 Jan;22(5):2722 2. [IF=1.813] Jiang Meng et al."Systems Pharmacology-Dissection of the Molecular Mechanisms of Dragon’s Blood in Improving Ischemic Stroke Prognosis."Evid-Based Compl Alt. 2020;2020:4858201 |
Propan-1-one, 1-(4-hydroxyphenyl)-3-(2,4,6-trimethoxyphenyl)- - Reference Information
| introduction | dragon's blood B is a chalcone compound derived from Dai medicine dragon's blood. some studies have found that dragon's blood B has strong analgesic activity. currently, dragon's blood B is mainly extracted from Dai medicine dragon's blood. |
| synthesis method | step 1: using 1,3, 5-trimethoxybenzene (I) as raw material, the reaction intermediate 2,4, 6-trimethoxybenzaldehyde (IV) is prepared by Vilsmeier-Haauc acylation reaction. In a 250ml three-mouth flask equipped with a stirrer and put into an ice bath, 8.76g(0.12mol)DMF is added, then 9.8g(0.064mol)POCl3 is slowly added to the three-mouth flask, after reaction for 0.5h to form a Vilsmeier complex, and then 10.10g(0.06mol)1,3, 5-trimethoxybenzene is slowly added to the complex reaction solution. Then remove the ice bath, install a condenser tube, move the reaction flask to a water bath at 30 ℃ for stirring for 3h to generate an intermediate, pour the intermediate reaction solution into a beaker filled with 60ml of ice water, stir and mix well with a glass rod, seal the beaker with a sealing film, put it into a refrigerator at 4 ℃ for cooling and crystallization, and take the next day to get 8.8g of rice white powder product with a yield of 74.68%. Step 2: Using p-hydroxyacetophenone (II) and benzyl chloride (III) as raw materials, the intermediate 4-benzyloxyacetophenone (V) is prepared by nucleophilic substitution reaction. At room temperature, DMF(50ml), p-hydroxyacetophenone (10g,0.0735mol), K2CO3(20.2g,0.147mol) and benzyl chloride (10.228g,0.0808mol) are sequentially added into a 250ml three-mouth flask equipped with a stirrer, then mixed and stirred at room temperature for 16h, after the reaction, the reaction mixture is poured into a beaker filled with 60ml of ice water, cooled, and then the precipitate is obtained, 16.2g of white powder target product can be obtained by drying, and the yield is 98.38%. Step 3: Using the reaction intermediates (IV) and (V) prepared in steps 1 and 2 as raw materials, the reaction intermediates 2,4, 6-trimethoxy -4 ′-benzyloxychalcone (VI) are prepared by Claisen-Schmidt condensation reaction. In a 100ml grinding mouth three-neck bottle equipped with a magnetic stirrer and a condenser tube, 10ml of methanol and 4-benzyloxyacetophenone (2.26g,0.01mol) are sequentially added, a solution prepared by 30ml of methanol and potassium hydroxide (2.80g,0.10mol) is added under stirring, heated to 50 ℃, and 2,4, 6-trimethoxybenzaldehyde (1.96g,0.01mol) is added after the bulk drug is dissolved, reflux is heated and TLC monitors the reaction until the reaction is complete. Stop the reaction, wait for cooling, suction and filtration, and dry the filter residue to obtain 3.60g of yellow powdered solid substance, which is the target product with 89% yield. Step 4: Catalytic hydrogenation of (VI) is reduced to 2,4, 6-trimethoxy -4 ′-hydroxydihydrochalcone (dragon blood B, VII). In a 100ml grinding mouth three-neck flask equipped with a magnetic stirrer and a condenser tube, methanol (25ml) and 2,4, 6-trimethoxy -4 '-benzyloxychalcone (1.9g,0.005mol) are sequentially added, ammonium formate (1.8g,0.03mol), Pd-C(0.2g) and methanol (25ml) are 10% under stirring, heated to reflux, and after the reaction is completed, palladium and carbon are filtered to remove, the filtrate is concentrated under reduced pressure to obtain light yellow oil, an appropriate amount of acetone is added to dissolve, excess ammonium formate is filtered to remove, and then concentrated under reduced pressure to obtain oil, vacuum drying to obtain light yellow solid substance, and column chromatography is used to separate and obtain white solid powder, namely dragon blood B1.11 g, with a yield of 70%. Longxue B, also known as 2,4, 6-trimethoxy-4 ′-hydroxydihydrochalcone, is a white powdery solid. |
| biological activity | Loureirin B (LB, LrB), flavonoids extracted from Dracaena cochinchinensis, is an inhibitor of PAI-1, and its IC50 value is 26.10 μM. Loureirin B downregulates p-ERK and p-JNK in TGF-β1 stimulated fibroblasts. Loureirin B mainly promotes insulin secretion by increasing Pdx-1, MafA and intracellular ATP levels, inhibiting KATP current and Ca2 + entering cells. |
| target | TargetValue p-ERK () p-JNK () Calcium Channel () Potassium Channel () PAI-1 () 26.10 μM |
| Target | Value |
| p-ERK () | |
| p-JNK () | |
| Calcium Channel () | |
| Potassium Channel () | |
| PAI-1 (Cell-free assay) | 26.10 μM |
| chemical properties | white powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from dragon blood tree resin. |
| use | dragon blood element B has analgesic and anti-inflammatory effects. used for content determination/identification/pharmacological experiment, etc. |
Last Update：2024-04-09 21:04:16
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Product Name: Loureirin B Visit Supplier Webpage Request for quotationCAS: 119425-90-0
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052
Wechat: 15671228036
Spot supply
Product Name: Loureirin B Visit Supplier Webpage Request for quotationCAS: 119425-90-0
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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