Xanthoxylin

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Names

[ CAS No. ]:
90-24-4

[ Name ]:
Xanthoxylin

[Synonym ]:
2-HYDROXY-4,6-DIMETHOXYACETOPHENONE
MFCD00017243
Brevifolin (VAN)
EINECS 201-978-3
4,6-Dimethoxy-2-hydroxyacetophenone
Phloracetophenone 4,6-Dimethyl Ether
2,4-Dimethoxy-6-hydroxyacetophenone
Acetophenone, 2'-hydroxy-4',6'-dimethoxy-
Ethanone, 1-(2-hydroxy-4,6-dimethoxyphenyl)-
1-(2-Hydroxy-4,6-dimethoxyphenyl)ethanone

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
355.1±37.0 °C at 760 mmHg

[ Melting Point ]:
80-84 °C(lit.)

[ Molecular Formula ]:
C₁₀H₁₂O₄

[ Molecular Weight ]:
196.200

[ Flash Point ]:
141.2±20.0 °C

[ Exact Mass ]:
196.073563

[ PSA ]:
55.76000

[ LogP ]:
2.37

[ Vapour Pressure ]:
0.0±0.8 mmHg at 25°C

[ Index of Refraction ]:
1.528

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36/37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2914509090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

2',4',6'-Trihydroxyacetophenone Monohydrate
Dimethyl sulfate
3,5-Dimethoxyphenol
Acetyl chloride
2',4',6'-Trimethoxyacetophenone
1,3,5-Trimethoxybenzene
o-Chloroacetophenone
DIEA
Methyl p-toluenesulfonate
methyl iodide

DownStream

2''-HYDROXY-3,4,4'',6''-TETRAMETHOXYCHALCONE
Ladanein
Flavokawain A
2',4',6'-Trihydroxyacetophenone Monohydrate
2',4'-Dihydroxy-6'-methoxyacetophenone
Luteolin
7,4'-Di-O-methylapigenin
3,5-Dimethoxyphenol
Chrysin
1-(3-bromo-2-hydroxy-4,6-dimethoxyphenyl)ethanone

Customs

[ HS Code ]: 2914509090

[ Summary ]:
HS:2914509090 other ketones with other oxygen function VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

Articles

Collateral sensitivity of resistant MRP1-overexpressing cells to flavonoids and derivatives through GSH efflux.

Biochem. Pharmacol. 90(3) , 235-45, (2014)

The multidrug resistance protein 1 (MRP1) is involved in multidrug resistance of cancer cells by mediating drug efflux out of cells, often in co-transport with glutathione (GSH). GSH efflux mediated b...

Antinociceptive action of 2-(4-bromobenzoyl)-3-methyl-4,6-dimethoxy benzofuran, a novel xanthoxyline derivative on chemical and thermal models of nociception in mice.

J. Pharmacol. Exp. Ther. 278(1) , 304-12, (1996)

The antinociceptive effect of the novel xanthoxyline derivative 2-(4-bromobenzoyl)-3-methyl-4-6-dimethoxy benzofuran) (BMDB), given i.p., p.o., s.c., subplantarly, intrathecally or by i.c.v. routes wa...

Synthesis of chalcone analogues with increased antileishmanial activity.

Bioorg. Med. Chem. 14(5) , 1538-45, (2006)

Eighteen analogues of an active natural chalcone were synthesized using xanthoxyline and some derivatives, and these analogues were tested for selective activity against both promastigotes and intrace...