Puerarin Chemical Properties

Melting point:

187-189°C

Boiling point:

688.0±55.0 °C(Predicted)

Density 

1.614±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

6.46±0.20(Predicted)

form 

Powder

color 

White to Off-white

Water Solubility 

Soluble in DMSO or DMF. Slightly soluble in water or ethanol

λmax

303nm(MeOH)(lit.)

BRN 

64198

InChIKey

HKEAFJYKMMKDOR-NCHCSYJDSA-N

SMILES

OC1=CC=C2C(C(C3C=CC(O)=CC=3)=COC2=C1[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)=O |&1:18,19,20,22,24,r|

LogP

0.408 (est)

CAS DataBase Reference

3681-99-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

F,C

Risk Statements 

11-34

Safety Statements 

22-24/25-45-36/37/39-26-16

WGK Germany 

3

RTECS 

UO5216000

F 

10

HS Code 

29389090

MSDS

• Language:English Provider:SigmaAldrich

Puerarin Usage And Synthesis

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.

Chemical Properties

White powder

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.

History

In 1959, Japanese chemist Shibata Shoji first studied the chemical production of pueraria root, indicating that isoflavones are the main active ingredients of pueraria root, including puerarin, daidzin and daidzein . Then in 2003, David Lee first total synthesized analogical puerarin . And it was in 1974 that puerarin was first extracted by Fang Qicheng and other chemists in China . Due to its strong activity of anti-cardiovascular and anti-cerebrovascular ischemia and hypoxia, expanding the coronary artery and cerebrovascular, reducing myocardial oxygen consumption, and improving myocardial systolic and microcirculation function, puerarin was approved for clinical use by the Ministry of Health in 1993.
In recent years, researchers have synthesized a series of puerarin derivatives, and active research showed that the part of the puerarin derivatives has a good biological activity and bioavailability. In a new dosage form research, researchers have developed several types of dosage forms such as quickrelease solid dispersions, solid from microemulsion preparation, etc., which greatly increase the solubility of puerarin, thus improving bioavailability. In recent years,the research on crystal drug has opened up new ways for the application of puerarin.

Uses

beta-adrenergic blocker

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.

Uses

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.

Definition

ChEBI: A hydroxyisoflavone that is isoflavone substituted by hydroxy groups at positions 7 and 4' and a beta-D-glucopyranosyl residue at position 8 via a C-glycosidic linkage.

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.

Biochem/physiol Actions

Isoflavone component of kudzu. Reduces anxiety symptoms associated with alcohol withdrawal.

Pharmacology

Contemporary pharmacological research has demonstrated that puerarin has wide pharmacological activities on the cardiovascular system, nervous system, liver impairments, osteoporosis and hangover .
The clinical and experimental researches have shown that puerarin has a significant role in the prevention of cerebral vascular disease, which can expand the coronary artery and improve the metabolism of an ischemic heart muscle, improving brain circulation, increasing cerebral blood flow and reducing blood volume and heart rate. There is good control of puerarin on myocardial ischemia and cerebral ischemic disease.
A large number of experiments have proved that puerarin can promote the glucose and lipid metabolism and reduce blood sugar and blood lipid. The protection of puerarin on diabetes was attributed to its functions on inhibiting apoptosis and oxidative stress.
Puerarin have protection efficacy on liver damage induced by chemical substances, alcohol, surgery and other experimental damage. This effect is closely related to the antioxidant effect, resisting lipid peroxidation, inhibiting platelet aggregation and improving circulation.
Puerarin can also improve the eye microcirculation obviously and reduce the pressure of the eyes, thus acting obvious therapeutic effect on glaucoma. In addition, it has a variety of preparations, such as liquors, which are still under development.

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.

Puerarin(3681-99-0)Related Product Information

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