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Puerarin

HCID 5281807
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Basic information

CAS
3681-99-0
Standard SMILES
O=c1c(-c2ccc(O)cc2)coc2c([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c(O)ccc12
InChIKey
HKEAFJYKMMKDOR-VPRICQMDSA-N
Molecular formula
C21H20O9
Average molar mass
416.4 g/mol
Monoisotopic mass
416.11073221

Overview

Puerarin is 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. It has a role as an autophagy inducer, a ferroptosis inhibitor, an antioxidant, an antipyretic, an anti-inflammatory agent, a plant metabolite and a cardioprotective agent. It is a C-glycosyl compound and a hydroxyisoflavone. It is functionally related to an isoflavone. It is a conjugate acid of a puerarin(1-).

Names & identifiers

Preferred name
Puerarin
IUPAC
7-hydroxy-3-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
English name
Puerarin
Molecular formula
C21H20O9
Molecular weight
416.38

Names & synonyms

Puerarin3681-99-0KakoneinDaidzein-8-C-glucosidePuerarin 80 mmDaidzein 8-c-glucosideNPI 031GCHEBI:8633DTXSID30958020Z9W89974167-hydroxy-3-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-oneNSC-380711
Show more names
PSYCHOSINEPurerarinDaidzeinePuerarinePUERARIN EXTRACTPueraria Root Flavone8-β-D-Glucopyranosyl-3-(4-hydroxyphenyl)-7-hydroxy-4H-1-benzopyran-4-one7-HYDROXY-3-[4-HYDROXYPHENYL]-1-BENZOPYRAN-4-ONE 8-[BETA-D-GLUCOPYRANOSIDEPuerain
4H-1-Benzopyran-4-one, 8-beta-D-glucopyranosyl-7-hydroxy-3-(4-hydroxyphenyl)-7-hydroxy-3-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]chromen-4-one7-hydroxy-3-(4-hydroxyphenyl)-8-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)chromen-4-one7-hydroxy-3-(4-hydroxyphenyl)-8-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl)chromen-4-oneRefChem:870306DTXCID0013859407-hydroxy-3-(4-hydroxyphenyl)-8-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-4H-chromen-4-oneAC1NQZ4N

Properties

Computed structural properties

XLogP
0
Topological polar surface area
157 Ų
Hydrogen bond donors
6
Hydrogen bond acceptors
9
Rotatable bonds
3
Heavy atoms
30
Formal charge
0
Complexity
659

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Isoflavonoids [PK1205]
LogP1.34
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section · 2 items

209.37 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

196.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
187 · 187-189°C
Boiling point
688 · 688.0±55.0 °C(Predicted)
Density
1.614 · 1.614±0.06 g/cm3(Predicted)
storage temp.
2 · 2-8°C
solubility
DMSO (Slightly), Methanol (Slightly)
pka
6.46 · 6.46±0.20(Predicted)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 50% (1 of 2) of reports.

Warning

H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (50%)

Safety data

F
10
PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
rtecs
UO5216000
hs_code
29389090
risk_code
11-34
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
F,C
safety_code
22-24/25-45-36/37/39-26-16
Storage Class
11 - Combustible Solids
Hazard statements
H302-H315-H319-H335
Precautionary statements
P261-P305+P351+P338

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationDrugs used to cause dilation of the blood vessels.
Applications · 5 items

DescriptionPuerarin, 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.

HistoryIn 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.

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Compound notes

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Database identifiers

CAS
3681-99-0
PubChem CID
5281807
DTXSID
DTXSID30958020
ChEMBL
CHEMBL486386
ChEBI
CHEBI:8633
UNII
Z9W8997416
EC Number
609-296-1
Nikkaji
J16.365A
form
Powder
color
White to Off-white
Water Solubility
Soluble in DMSO or DMF. Slightly soluble in water or ethanol
λmax
303 nm · 303nm(MeOH)(lit.)
BRN
64198 · 64198
Cosmetics Ingredients Functions
ANTIOXIDANT
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 · 0.408 (est)
CAS DataBase Reference
3681 · 3681-99-0(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
9 W8997416 · Z9W8997416
UNSPSC Code
41116107 · 41116107
NACRES
77 · NA.77
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H315-H319-H335
Precautionary statements
261 · P261-P305+P351+P338
PPE
95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes
F,C
Risk Statements
11 · 11-34
Safety Statements
22 · 22-24/25-45-36/37/39-26-16
WGK Germany
3 · 3
RTECS
5216000 · UO5216000
F
10 · 10
HS Code
29389090 · 29389090
Storage Class
11 · 11 - Combustible Solids

Usesbeta-adrenergic blocker

UsesPuerarin 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.

UsesPuerarin 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.

Upstream & downstream products

Upstream raw materials

7-methoxy-3-(4-methoxyphenyl)-8-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-4H-chromen-4-one

Additional notes

DefinitionChEBI: 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.