Puerarin

Base Information

• Chemical Name: Puerarin
• CAS No.: 3681-99-0
• Molecular Formula: C21H20O9
• Molecular Weight: 416.384
• Hs Code.: 29389090
• European Community (EC) Number: 609-296-1
• Wikipedia: Puerarin
• Wikidata: Q104250649
• Mol file: 3681-99-0.mol

Synonyms:7-hydroxy-3-(4-hydroxyphenyl)-8-[(2S,3S,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one;Hexitol, 1,5-anhydro-1-C-[7-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-8-yl]-;Pneranin;NPI 031G;4H-1-Benzopyran-4-one, 8-beta-D-glucopyranosyl-7-hydroxy-3-(4-hydroxyphenyl)- (9CI);8-beta-D-Glucopyranosyl-7-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one;Sanguinarine citrate;Puerarin 99% (UV);Puerariae P.E.;Pueraria lobata;Pueraria P.E;

Chemical Property of Puerarin

Chemical Property:

• Appearance/Colour: Yellow brown Fine Powder
• Vapor Pressure: 7.06E-20mmHg at 25°C
• Melting Point: 187-189 °C
• Refractive Index: 1.719
• Boiling Point: 791.2 °C at 760 mmHg
• PKA: 6.46±0.20(Predicted)
• Flash Point: 281.5 °C
• PSA: 160.82000
• Density: 1.642 g/cm³
• LogP: 0.38610
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in DMSO or DMF. Slightly soluble in water or ethanol
• XLogP3: 0
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 416.11073221
• Heavy Atom Count: 30
• Complexity: 659

Purity/Quality:

98%, ^*data from raw suppliers

Puerarin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,C
• Hazard Codes: F,C
• Statements: 11-34
• Safety Statements: 22-24/25-45-36/37/39-26-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=COC3=C(C2=O)C=CC(=C3C4C(C(C(C(O4)CO)O)O)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1C2=COC3=C(C2=O)C=CC(=C3[C@H]4[C@H](C([C@@H](C(O4)CO)O)O)O)O)O
• Recent ClinicalTrials: Effect of Puerarin on Heart Health in Men
• Description: Puerarin, also known as pueraria flavonoids, is a kind of flavonoid glycoside extracted from the roots of Pueraria alba or Pueraria thomsonii and is also one of the main effective ingredients of Pueraria lobata. That Pueraria lobate was used to treat diseases has already been recorded in China’s ancient medical books such as Shen Nong’s Materia Medica, Treatise on Miscellaneous Diseases and Medical Dictionary. Kanzu root is widely distributed in our country and of rich resources. It has been reported that puerarin could be extracted from Pueraria lobata (Wild.) Ohwi, Radix Pueraria thomsonii, Pueraria omeiensiswanget Tang, Pueraria edulis Pamp and Pueraria phaseoloides, but the content of puerarin differs. Pueraria has a great value for nutrition and medicine and was considered the south ginseng of China. Puerarin has been widespread concerned over our country for its use of food and medicine in recent years.
• Physical properties: Appearance: White to light-yellow crystalline powder. Solubility: Soluble in methanol, freely soluble in ethanol, slightly soluble in water, insoluble in chloroform and ether. Melting point: 187–189?°C.
• Uses: Puerarin is a natural isoflavone isolated from plants of the genus Pueraria used in traditional Chinese herbal medicine. It is biotransformed by intestinal bacteria to give the phytoestrogens daidzein and equol , resulting in antithrombotic, antiallergic, and other salutary effects. When given intraperitoneally, puerarin evokes diverse responses by modulating serotonin receptors. This compound also suppresses lipopolysaccharide-mediated activation of NF-κB in RAW 264.6 macrophages when given at 20-40 μM. beta-adrenergic blocker Puerarin is a naturally occuring isoflavonoid derived from Chinese medical herb kudzu root and has been used for the treatment of various cardiovascular diseases. Recent sutdies have shown the potenti al of puerarin treatment as a novel approach to lowering the risk of or improving function in ischemia-reperfusion brain injury-related disorders.
• Indications: At present the most widely used medicinal formulation of puerarin in clinical application is puerarin injection, with more than 90 enterprises producing it. The injection was mainly used for the treatment of coronary heart disease, angina pectoris, myocardial infarction, retinal movement, vein occlusion, sudden deafness and other diseases. Another dosage form of puerarin is eye drops for the treatment of primary open-angle glaucoma, ocular hypertension, primary angle closure glaucoma and secondary glaucoma. In addition, there are puerarin tablets and puerarin capsules, belonging to the health-care product.
• Clinical Use: Currently, puerarin is used clinically for the treatment of hypertension, coronary heart disease, angina pectoris, arrhythmia, myocardial infarction, ischemic cerebrovascular disease, retinal arteriovenous obstruction, sudden deafness, diabetes complications, dizziness and other diseases. Besides, it also is used to treat chronic pharyngitis, cerebral infarction and Parkinson’s syndrome. However, puerarin also has adverse reactions in clinical therapy. Fever is the main symptom. In addition, allergic dermatitis, anaphylactic shock, laryngeal oedema, increased transaminase, gastrointestinal bleeding, haemolysis phenomenon and kidney damage occurred occasionally, and these symptoms disappeared after withdrawal of the medication.

Technology Process of Puerarin

There total 11 articles about Puerarin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

7-hydroxy-4'-methoxy-8-C-(2,3,4,6-tetra-O-benzyl-β-D-glucocopyranosyl)isoflavone → puerarin (3681-99-0)

Guidance literature:

7-hydroxy-4'-methoxy-8-C-(2,3,4,6-tetra-O-benzyl-β-D-glucocopyranosyl)isoflavone; With boron tribromide; In dichloromethane; at -78 ℃; for 0.5h; Inert atmosphere;

With methanol; In dichloromethane; at 0 ℃; for 0.0833333h; Inert atmosphere;

DOI:10.1080/07328303.2018.1496253

Reference yield: 75.0%

6-[7-hydroxy-3-(4-hydroxy-phenyl)-4-oxo-4H-chromen-8-yl]-3,4,5-tris-trimethyl-silanyloxy-tetrahydro-pyran-2-carbaldehyde (1029605-74-0) → puerarin (3681-99-0)

Guidance literature:

6-[7-hydroxy-3-(4-hydroxy-phenyl)-4-oxo-4H-chromen-8-yl]-3,4,5-tris-trimethyl-silanyloxy-tetrahydro-pyran-2-carbaldehyde; With sodium tetrahydroborate; In tetrahydrofuran; ethanol; at 0 ℃; for 0.166667h;

With hydrogenchloride; In tetrahydrofuran; ethanol; at 0 - 20 ℃; for 0.25h; Further stages.;

DOI:10.1002/jlcr.1398

Reference yield: 71.0%

4',7-di-O-benzyldaidzein 8-C-β-D-(2,3,4,6-tetra-O-benzylglucoside) (1242241-66-2) → puerarin (3681-99-0)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.bmcl.2010.06.077

upstream raw materials:

Malonic acid mono-{(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-[7-hydroxy-3-(4-hydroxy-phenyl)-4-oxo-4H-chromen-8-yl]-tetrahydro-pyran-2-ylmethyl} ester

4',7-di-O-methyl-puerarin

6-[7-hydroxy-3-(4-hydroxy-phenyl)-4-oxo-4H-chromen-8-yl]-3,4,5-tris-trimethyl-silanyloxy-tetrahydro-pyran-2-carbaldehyde

Acetic acid (2S,3S,4R,5R,6R)-4,5-diacetoxy-2-{2-acetoxy-6-methoxy-3-[(E)-3-(4-methoxy-phenyl)-acryloyl]-phenyl}-6-acetoxymethyl-tetrahydro-pyran-3-yl ester

Downstream raw materials:

7-hydroxy-3-(4-trimethylsilanyloxy-phenyl)-8-(3,4,5-tris-trimethylsilanyloxy-6-trimethylsilanyloxy-methyl-tetrahydro-pyran-2-yl)-chromen-4-one

4',7-di-O-methyl-puerarin

Refernces

• 1、 Zhang, Hai-Jiang,Yang, Xiao-Ping,Wang, Kui-Wu. "Isolation of two new C-glucofuranosyl isoflavones from Pueraria lobata (Wild.) Ohwi with HPLC-MS guiding analysis". . p. 293 - 299. Retrieved 2010.
• 2、 Kato, Eisuke,Kawabata, Jun. "Glucose uptake enhancing activity of puerarin and the role of C-glucoside suggested from activity of related compounds". supporting information; experimental part. p. 4333 - 4336. Retrieved 2010/09/18.