Name: Gossypin
SKU: 652-78-8

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Basic Information

Molecular Structure:
CAS No.:	652-78-8
Name:	Gossypin

Formula:	C₂₁H₂₀O₁₃
Molecular Weight:	480.382
Synonyms:	2-(3,4-Dihydroxyphenyl)-8-(beta-D-glucopyranosyloxy)-3,5,7-trihydroxy-4H-1-benzopyran-4-one;3,5,7,8,3',4'-Hexahydroxyflavone-8-glucoside;Gossypetin-8-glucoside;
Density:	1.883 g/cm³
Melting Point:	229-230 ºC
Boiling Point:	886 °C at 760 mmHg
Flash Point:	310.8 °C
Hazard Symbols:	XiXn
Risk Codes:	36/37/38-62-37/38-36-22
Safety:	26-36-37
PSA:	230.74000
LogP:	-0.83330

Synthetic route

: Gossypetin-3-β-D-(2-O-β-D-glucopyranosidoglucopyranosid)-8-β-D-glucopyranosid

: 652-78-8
gossypin

Conditions

Conditions	Yield
With hydrogenchloride In ethanol at 70℃; for 1h;

: 98-01-1
furfural

: 652-78-8
gossypin

: 1283102-52-2
2-(9-(2-furyl)-4,5-dihydroxy-7-(3,5,7-trihydroxy-8-{(3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-2-pyranyl)oxy}-4-oxo-4H-2-chromenyl)-9H-2-xanthenyl)-3,5,7-trihydroxy-8-{(3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-2-pyranyl)oxy}-4H-4-chromenone

Conditions

Conditions	Yield
With iron(III) chloride at 130 - 140℃;

: 98-03-3
thiophene-2-carbaldehyde

: 652-78-8
gossypin

: 1283102-55-5
2-(4,5-dihydroxy-9-(2-thienyl)-7-(3,5,7-trihydroxy-8-{(3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-2-pyranyl)oxy}-4-oxo-4H-2-chromenyl)-9H-2-xanthenyl)-3,5,7-trihydroxy-8-{(3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-2-pyranyl)oxy}-4H-4-chromenone

Conditions

Conditions	Yield
With iron(III) chloride at 130 - 140℃;

: 555-16-8
4-nitrobenzaldehdye

: 652-78-8
gossypin

: 1283102-51-1
2-(4,5-dihydroxy-9-(4-nitrophenyl)-7-(3,5,7-trihydroxy-8-{(3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-2-pyranyl)oxy}-4-oxo-4H-2-chromenyl)-9H-2-xanthenyl)-3,5,7-trihydroxy-8-{(3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-2-pyranyl)oxy}-4H-4-chromenone

Conditions

Conditions	Yield
With iron(III) chloride at 130 - 140℃;

: 100-52-7
benzaldehyde

: 652-78-8
gossypin

: 1283102-43-1
2-(4,5-dihydroxy-9-phenyl-7-(3,5,7-trihydroxy-8-{(3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-2-pyranyl)oxy}-4-oxo-4H-2-chromenyl)-9H-2-xanthenyl)-3,5,7-trihydroxy-8-{(3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-2-pyranyl)oxy}-4H-4-chromenone

Conditions

Conditions	Yield
With iron(III) chloride at 130 - 140℃;

: 123-08-0
4-hydroxy-benzaldehyde

: 652-78-8
gossypin

: 1283102-47-5
2-(4,5-dihydroxy-9-(4-hydroxyphenyl)-7-(3,5,7-trihydroxy-8-{(3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-2-pyranyl)oxy}-4-oxo-4H-2-chromenyl)-9H-2-xanthenyl)-3,5,7-trihydroxy-8-{(3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-2-pyranyl)oxy}-4H-4-chromenone

Conditions

Conditions	Yield
With iron(III) chloride at 130 - 140℃;

: 123-11-5
4-methoxy-benzaldehyde

: 652-78-8
gossypin

: 1283102-45-3
2-(4,5-dihydroxy-9-(4-methoxyphenyl)-7-(3,5,7-trihydroxy-8-{(3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-2-pyranyl)oxy}-4-oxo-4H-2-chromenyl)-9H-2-xanthenyl)-3,5,7-trihydroxy-8-{(3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-2-pyranyl)oxy}-4H-4-chromenone

Conditions

Conditions	Yield
With iron(III) chloride at 130 - 140℃;

: 90-02-8
salicylaldehyde

: 652-78-8
gossypin

: 1283102-48-6
2-(4,5-dihydroxy-9-(2-hydroxyphenyl)-7-(3,5,7-trihydroxy-8-{(3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-2-pyranyl)oxy}-4-oxo-4H-2-chromenyl)-9H-2-xanthenyl)-3,5,7-trihydroxy-8-{(3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-2-pyranyl)oxy}-4H-4-chromenone

Conditions

Conditions	Yield
With iron(III) chloride at 130 - 140℃;

: 100-83-4
meta-hydroxybenzaldehyde

: 652-78-8
gossypin

: 1283102-50-0
2-(4,5-dihydroxy-9-(3-hydroxyphenyl)-7-(3,5,7-trihydroxy-8-{(3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-2-pyranyl)oxy}-4-oxo-4H-2-chromenyl)-9H-2-xanthenyl)-3,5,7-trihydroxy-8-{(3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-2-pyranyl)oxy}-4H-4-chromenone

Conditions

Conditions	Yield
With iron(III) chloride at 130 - 140℃;

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Specification

With CAS Registry Number 652-78-8, Gossypin is also can be called 2-(3,4-Dihydroxyphenyl)-8-(beta-D-glucopyranosyloxy)-3,5,7-trihydroxy-4H-1-benzopyran-4-one ; 3,5,7,8,3',4'-Hexahydroxyflavone-8-glucoside ; Gossypetin-8-glucoside ,and its IUPAC Name is 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one . It belongs to the product category of flavanols.

Properties of Gossypin: (1)Index of Refraction: 1.799; (2)Molar Refractivity: 109.02 cm³; (3)Molar Volume: 255 cm³; (4)Surface Tension: 127.8 dyne/cm; (5)Density: 1.883 g/cm³; (6)Flash Point: 310.8 °C ; (7)Melting Point: 229-230 °C; (8)Enthalpy of Vaporization: 134.9 kJ/mol; (9)Boiling Point: 886 °C at 760 mmHg; (10)Vapour Pressure: 1.18E-33 mmHg at 25 °C.

A study investigated that percutaneous administration of SM induces oxidative stress and gossypin can protect it as a prophylactic agent by intraperitoneal or oral routes. Both gossypin and suramin inhibited (P<0.001) compound 48/80-induced systemic anaphylaxis reactions, antiprurities (P<0.001) and reduced the histamine release in rats. Further, both showed significant (P<0.001) protection against rat peritoneal mast cells activated by compound 48/80. Thus, our findings provide evidence that gossypin and suramin inhibit mast cell-derived allergic reactions. In addition, another study shows that the influence of gossypin on the development of acute tolerance to morphine was investigated using acetic acid induced writhing assay procedure in mice. Gossypin pre-treatment significantly attenuated the acute tolerance development to morphine induce antinociceptive response. All these evidences suggest that the therapeutic potential of gossypin as a substitute to morphine.

When you are using Gossypin, please be cautious about it as the following:
First: Wear suitable protective clothing and gloves because it is irritating to eyes, respiratory system and skin. And Gossypin is risk of impaired fertility and harmful if swallowed, so you should in case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

The toxicity of Gossypin as the following:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
guinea pig	LD50	intravenous	26300ug/kg (26.3mg/kg)	Arzneimittel-Forschung. Drug Research. Vol. 9, Pg. 647, 1959.
rat	LD50	intraperitoneal	2240mg/kg (2240mg/kg)	Indian Journal of Pharmacology. Vol. 10, Pg. 277, 1978.
rat	LD50	intravenous	125mg/kg (125mg/kg)	Arzneimittel-Forschung. Drug Research. Vol. 9, Pg. 647, 1959.

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