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Gossypin
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Name

Gossypin

 EINECS N/A
CAS No. 652-78-8 Density 1.883 g/cm3
PSA 230.74000 LogP -0.83330
Solubility N/A Melting Point 229-230 ºC
Formula C21H20O13 Boiling Point 886 °C at 760 mmHg
Molecular Weight 480.382 Flash Point 310.8 °C
Transport Information N/A Appearance N/A
Safety 26-36-37 Risk Codes 36/37/38-62-37/38-36-22
Molecular Structure Molecular Structure of 652-78-8 (Gossypin) Hazard Symbols IrritantXiHarmfulXn
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;

Article Data 1

Gossypin Synthetic route

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

652-78-8

gossypin

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

Gossypin 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) Effect 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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