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Isorhamnetin

Isorhamnetin structure

CAS No:
480-19-3
Formula:
C16H12O7
Chemical Name:
Isorhamnetin
Synonyms:
4H-1-Benzopyran-4-one,3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-;Flavone,3,4′,5,7-tetrahydroxy-3′-methoxy-;Isorhamnetin;3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one;C.I. 75680;Isorhamnetol;3′-Methoxyquercetin;3′-O-Methylquercetin;Quercetin 3′-methyl ether;3,4′,5,7-Tetrahydroxy-3′-methoxyflavone;3′-Methylquercetin;3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one;98006-95-2
Categories:
Cosmetic Ingredient > Skin Protecting

Description

Isorhamnetin is a flavonoid compound extracted from the Chinese herb Hippophae rhamnoides L.. Isorhamnetin suppresses skin cancer through direct inhibition of MEK1 and PI3K.

Solid

Isorhamnetin is a monomethoxyflavone that is quercetin in which the hydroxy group at position 3' is replaced by a methoxy group. It has a role as an EC 1.14.18.1 (tyrosinase) inhibitor, an anticoagulant and a metabolite. It is a 7-hydroxyflavonol, a tetrahydroxyflavone and a monomethoxyflavone. It derives from a quercetin. It is a conjugate acid of an isorhamnetin(1-).

Isorhamnetin Basic Attributes

Molecular Weight：

316.26

Exact Mass：

316.26

EC Number：

207-545-5

UNII：

07X3IB4R4Z

DSSTox ID：

DTXSID10197379

HScode：

29329990

Characteristics

PSA：

116

XLogP3：

1.9

Appearance：

Solid

Density：

1.6±0.1 g/cm3

Melting Point：

305 °C (decomp)

Boiling Point：

599.4°C at 760 mmHg

Flash Point：

227.8±23.6 °C

Refractive Index：

1.741

Water Solubility：

1122 mg/L @ 25 °C (est)

Storage Conditions：

2-8°C

Vapor Pressure：

5.79E-15mmHg at 25°C

Collision Cross Section：

172.96 Å² [M+H]+ [CCS Type: DT, Method: stepped-field]|195.91 Å² [M+Na]+ [CCS Type: DT, Method: stepped-field]|174.6 Å² [M-H]- [CCS Type: DT, Method: stepped-field]|174 Å² [M-H]-

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38-40

safety instructions：

22-36-26-36/37

RTECS Number：

LK9275450

Marks：

Xi,Xn

Precautionary statement(s)：

P280

Hazard Statements：

H351

Drug Information

Metabolism/Metabolites：

Isorhamnetin has known human metabolites that include (2S,3S,4S,5R)-6-[5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid.

MeSH Entry Terms：

3,4',5,7-tetrahydroxy-3'-methoxy-flavone

Isorhamnetin Use and Manufacturing

Uses

Isorhamnetin is a natural flavonol aglycone that is the 3-methyl metabolite of quercetin . It has antioxidant activity and inhibits xanthine oxidase (IC50 = 0.40 μM). Isorhamnetin also competitively inhibits the human multidrug and toxic compounds extrusion transporter 1 (Ki = 0.32 μM), which has an important role in the excretion of xenobiotics at the kidney and liver. It has also been reported to potentiate the neurological actions of nerve growth factor, diminish the cardiotoxic impact of doxorubicin, and have beneficial anti-cancer effects.

Use Classification：

Polyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]

Computed Properties

Molecular Weight:316.26
XLogP3:1.9
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:2
Exact Mass:316.05830272
Monoisotopic Mass:316.05830272
Topological Polar Surface Area:116
Heavy Atom Count:23
Complexity:503
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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CAS No.: 480-19-3

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Guide of Isorhamnetin

Description
Basic Attributes
Characteristics
Safety Information
Drug Information
Use and Manufacturing
Computed Properties
Recommended Suppliers
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Isorhamnetin

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