3D Mol Similar

Puerarin

Iupac Name：7-hydroxy-3-(4-hydroxyphenyl)-8-[(3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one

CAS No.：3681-99-0

Molecular Weight：416.382

Introduction: beta-adrenergic blocker View more+

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1. Names and Identifiers

1.1 Name: Puerarin
1.2 Synonyms: 4-19-00-03200 4H-1-Benzopyran-4-one, 8-(Β-D-glucopyranosyloxy)-7-hydroxy-3-(4-hydroxyphenyl)- 4H-1-Benzopyran-4-one,8-β-D-glucopyranosyl- 7-Hydroxy-3-(4-hydroxyphényl)-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxyméthyl)tétrahydro-2H-pyran-2-yl]oxy}-4H-chromén-4-one 7-hydroxy-3-(4-hydroxyphenyl)- 7-Hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl b-D-glucopyranoside 7-Hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl Β-D-glucopyranoside 7-Hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl-Β-D-glucopyranoside 7-Hydroxy-3-(4-hydroxyphenyl)-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-4H-chromen-4-on 7-Hydroxy-3-(4-hydroxyphenyl)-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-4H-chromen-4-one 7-HYDROXY-3-[4-HYDROXYPHENYL]-1-BENZOPYRAN-4-ONE 8-[BETA-D-GLUCOPYRANOSIDE 8-(Β-D-Glucopyranosyl)-4',7-dihydroxyisoflavone 8-GLUCOSYLDAIDZEIN daidzein-8-C-glucose DAIDZEIN-8-C-GLUCOSIDE Kakonein MFCD00076007 PSYCHOSINE Puararin Puerain Pueraria flavonoids PUERARIAROOT.P.E PUERARIN EXTRACT Puerarin std. Puerarine Puerqarin Purerarin

1.3 CAS No.: 3681-99-0

1.4 CID: 5281807

1.5 EINECS(EC#): 609-296-1

1.6 Molecular Formula: C21H20O9 (isomer)

1.7 Inchi: InChI=1S/C21H20O9/c22-7-14-17(26)18(27)19(28)21(30-14)15-13(24)6-5-11-16(25)12(8-29-20(11)15)9-1-3-10(23)4-2-9/h1-6,8,14,17-19,21-24,26-28H,7H2/t14-,17-,18+,19-,21+/m1/s1

1.8 InChkey: HKEAFJYKMMKDOR-VPRICQMDSA-N

1.9 Canonical Smiles: C1=CC(=CC=C1C2=COC3=C(C2=O)C=CC(=C3C4C(C(C(C(O4)CO)O)O)O)O)O

1.10 Isomers Smiles: C1=CC(=CC=C1C2=COC3=C(C2=O)C=CC(=C3[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O

2. Properties

3.1 Density: 1.642

3.1 Melting point: 187-189℃

3.1 Boiling point: 791.2 °C at 760 mmHg

3.1 Refractive index: 1.719

3.1 Flash Point: 281.5 °C

3.1 Precise Quality: 416.11100

3.1 PSA: 160.82000

3.1 logP: 0.38610

3.1 Λmax: 303nm(MeOH)(lit.)

3.2 Appearance: Yellow brown Fine Powder

3.3 Chemical Properties: White powder

3.4 Color/Form: Powder

3.5 pKa: 6.46±0.20(Predicted)

3.6 Water Solubility: Soluble in water and ethanol

3.7 StorageTemp: 2-8°C

3. Use and Manufacturing

4.1 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. PuerarinSupplier

4.2 GHS Classification: Signal: Warning
GHS Hazard Statements
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501

4.3 Storage: Ambient temperatures.

4.4 Usage: beta-adrenergic blocker

4. Safety and Handling

5.1 Hazard Codes: F; C

5.1 Risk Statements: R11

5.1 Safety Statements: S22;S24/25

5.1 RIDADR: NONH for all modes of transport

5.1 WGK Germany: 3

5.1 RTECS: UO5216000

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. Synthesis Route

3681-99-0Total: 4 Synthesis Route

69667-95-4

3681-99-0 470 Suppliers

Literatures:
Lee, David Y. W.; Zhang, Wu-Yan; Karnati, Vishnu Vardhan R. Tetrahedron Letters, 2003 , vol. 44, # 36 p. 6857 - 6859
Yield: null

147899-32-9

3681-99-0 470 Suppliers

Literatures:
Park; Hakamatsuka; Noguchi; Sankawa; Ebizuka Chemical and Pharmaceutical Bulletin, 1992 , vol. 40, # 7 p. 1978 - 1980
Yield: null

1029605-74-0

3681-99-0 470 Suppliers

Literatures:
Lee; Ji; Zhang Journal of Labelled Compounds and Radiopharmaceuticals, 2007 , vol. 50, # 8 p. 702 - 705
Yield: ~76%

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7. Other Information

7.0 Usage: Thought to interfere with the synthesis of mycolic acids, an essential fatty acid component found in Mycobacterium cell walls

7.1 BRN: 64198

7.2 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.

7.3 Chemical Properties: White powder

7.4 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.

7.5 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.

7.6 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.

7.7 Uses: beta-adrenergic blocker

7.8 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.

7.9 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.

7.10 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.

7.11 Biochem/physiol Actions: Isoflavone component of kudzu. Reduces anxiety symptoms associated with alcohol withdrawal.

7.12 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.

7.13 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.

8. Computational chemical data

Molecular Weight：416.382g/mol
Molecular Formula：C₂₁H₂₀O₉
Compound Is Canonicalized：True
XLogP3-AA：0
Exact Mass：416.11073221
Monoisotopic Mass：416.11073221
Complexity：659
Rotatable Bond Count：3
Hydrogen Bond Donor Count：6
Hydrogen Bond Acceptor Count：9
Topological Polar Surface Area：157
Heavy Atom Count：30
Defined Atom Stereocenter Count：5
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1

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