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Gossypol

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Name

Gossypol

EINECS 636-899-7
CAS No. 303-45-7 Density 1.403 g/cm3
PSA 155.52000 LogP 6.38220
Solubility Soluble in 100%ethanol (25 mg/ml), DMF (25 mg/ml), acetone, DMSO (25 mM), methanol (2 mg/ml), ether, chloroform, sodium carbonate, and dilute aqueous solutions of ammonia . Insoluble in water. Gossypol is a male antifertility agent with antispermatogenic activity and has been shown to contain antitumor, anitviral, and antioxidant properties. Melting Point 181-183 °C
Formula C30H30O8 Boiling Point 707.888 °C at 760 mmHg
Molecular Weight 518.563 Flash Point 395.872 °C
Transport Information N/A Appearance N/A
Safety 22-36-36/37/39-27-26 Risk Codes 22-40-36/37/38
Molecular Structure Molecular Structure of 303-45-7 (GOSSYPOL) Hazard Symbols IrritantXi, HarmfulXn
Synonyms

[2,2'-Binaphthalene]-8,8'-dicarboxaldehyde,1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl- (8CI);1,1',6,6',7,7'-Hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-2,2'-binaphthalene-8,8'-dicarboxaldehyde;1,6,7,1',6',7'-Hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-8,8'-dicarboxaldehyde;2,2'-Bis[1,6,7-trihydroxy-3-methyl-5-isopropyl-8-aldehydonaphthyl];2,2'-Bis[8-formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthyl];BL 193;NSC 56817;NSC 624336;No Fertil;Pogosin;Tash 1;

Article Data 16

Gossypol Synthetic route

5453-04-3, 866541-93-7, 1189561-66-7

(±)-gossypol acetic acid

303-45-7

(rac)-gossypol

Conditions
ConditionsYield
With iron(III) chloride In acetone at 60℃;85%
In diethyl ether; water at 25℃; for 0.166667h; Temperature; Solvent; Sonication;105 mg
40817-07-0

2,3,8-trihydroxy-4-isopropyl-6-methyl-1-naphthaldehyde

303-45-7

(rac)-gossypol

Conditions
ConditionsYield
With tert-butyl peroxyacetate In 1,2-dichloro-ethane at 80℃; for 4h; Inert atmosphere;76.1%
With tert-butyl peroxyacetate In 1,2-dichloro-ethane at 80℃; for 2.5h; Temperature; Inert atmosphere;52%
With tert-butyl peroxyacetate In 1,2-dichloro-ethane; mineral oil at 80℃; for 2.5h; Inert atmosphere; Schlenk technique;41%
With laccase of Coriolus versicolor; oxygen at 30℃; pH=5.5; aq. phosphate buffer;
784206-41-3

apogossypol

864131-95-3

N,N'-diphenylformamidine

303-45-7

(rac)-gossypol

Conditions
ConditionsYield
With hydroquinone at 180℃; under 5 - 15 Torr; for 2.5h;72%
784206-41-3

apogossypol

303-45-7

(rac)-gossypol

Conditions
ConditionsYield
With Dichloromethyl methyl ether; titanium tetrachloride In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere;37%
73728-76-4

4,4'-dihydroxy-5,5'-diisopropyl-7,7'-dimethyl-bis(3H-naphtho[1,8-bc]furan-3-one)

303-45-7

(rac)-gossypol

Conditions
ConditionsYield
In water; acetone for 48h;
Conditions
ConditionsYield
With hydrogenchloride In ethanol at 25℃; Kinetics; Mechanism; Thermodynamic data; other temperatures, ΔH(excit.), ΔS(excit.), ΔG(excit.);
7664-93-9

sulfuric acid

6952-36-9

dianilogossipol

303-45-7

(rac)-gossypol

3-(1H-indol-3-yl)-2-[(1,6,1',6'-tetrahydroxy-8'-{[2-(1H-indol-3-yl)-1-methoxycarbonyl-ethylamino]-methylene}-5,5'-diisopropyl-3,3'-dimethyl-7,7'-dioxo-7',8'-dihydro-7H-[2,2']binaphthalenyl-8-ylidenemethyl)-amino]-propionic acid methyl ester

303-45-7

(rac)-gossypol

Conditions
ConditionsYield
With hydrogenchloride; acetic acid In diethyl ether Heating;

C54H54N4O10

303-45-7

(rac)-gossypol

Conditions
ConditionsYield
With hydrogenchloride; acetic acid In diethyl ether Heating;

4-isopropyl-3,8-dimethoxy-1,6-dimethylnaphthalen-2-ol

303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: silver(l) oxide / methanol / 3 h / 20 °C
2: potassium carbonate / acetone / 5 h / 20 °C
3: dichloromethane / 0.5 h / 20 °C
4: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
6: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
7: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 7 steps
1: silver(l) oxide / 2 h / Reflux
2: potassium carbonate / acetone / 5 h / 20 °C
3: dichloromethane / 0.5 h / 20 °C
4: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
6: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
7: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 8 steps
1: silver(l) oxide / methanol / 3 h / 20 °C
2: potassium carbonate / acetone / 5 h / 20 °C
3: dichloromethane / 0.5 h / 20 °C
4: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
6: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
7: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
8: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 8 steps
1: silver(l) oxide / 2 h / Reflux
2: potassium carbonate / acetone / 5 h / 20 °C
3: dichloromethane / 0.5 h / 20 °C
4: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
6: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
7: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
8: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme

Gossypol Consensus Reports

EPA Genetic Toxicology Program.

Gossypol Specification

The Gossypol, with the CAS registry number 303-45-7, is also known as 2,2'-Bis(8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene). It belongs to the product categories of Aromatic Phenols; Antitumour. This chemical's molecular formula is C30H30O8 and molecular weight is 518.55. What's more, its IUPAC name is called 7-(8-Formyl-1,6,7-trihydroxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)-2,3,8-trihydroxy-6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde. Gossypol is a natural phenol derived from the cotton plant (genus Gossypium). Gossypol is a phenolic aldehyde that permeates cells and acts as an inhibitor for several dehydrogenase enzymes. It is a yellow pigment. And this chemical should be kept in a cold, dry place.

Physical properties about Gossypol are: (1)ACD/LogP: 5.42; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): 5.405; (4)ACD/LogD (pH 7.4): 4.795; (5)ACD/BCF (pH 5.5): 7488.263; (6)ACD/BCF (pH 7.4): 1838.539; (7)ACD/KOC (pH 5.5): 20462.531; (8)ACD/KOC (pH 7.4): 5024.019; (9)#H bond acceptors: 8; (10)#H bond donors: 6; (11)#Freely Rotating Bonds: 11; (12)Polar Surface Area: 155.52 Å2; (13)Index of Refraction: 1.742; (14)Molar Refractivity: 149.345 cm3; (15)Molar Volume: 369.555 cm3; (16)Surface Tension: 71.297 dyne/cm; (17)Density: 1.403 g/cm3; (18)Flash Point: 395.872 °C; (19)Enthalpy of Vaporization: 107.239 kJ/mol; (20)Boiling Point: 707.888 °C at 760 mmHg; (21)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of Gossypol: it is a polyphenol derived from the cotton plant (genus Gossypium, family Malvaceae). It is formed metabolically through acetate via the isopernoid pathway.

 Gossypol is formed metabolically through acetate via the isopernoid pathway.

Uses of Gossypol: it is used to produce other chemicals. For example, it can react with Ethylamine to get 1,6,7,1',6',7'-Hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthyl-8,8'-dicarbaldehyde bis-ethylimine. The reaction occurs with solvents diethyl ether, propan-2-ol at temperature of 20-45 °C. The yield is 96 %.

Gossypol can react with Ethylamine to get 1,6,7,1',6',7'-Hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthyl-8,8'-dicarbaldehyde bis-ethylimine.

When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system or other mucous membranes. If swallowed, it's harmful to health. It may cause damage to health. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. And you must take off immediately all contaminated clothing. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: Cc1cc2c(c(c(c(c2C(C)C)O)O)C=O)c(c1c3c(cc4c(c3O)c(c(c(c4C(C)C)O)O)C=O)C)O
(2) InChI: InChI=1S/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3
(3) InChIKey: QBKSWRVVCFFDOT-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
pig LD50 oral 550mg/kg (550mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Journal of the American Oil Chemists' Society. Vol. 40, Pg. 571, 1963.
rat LD50 oral 2315mg/kg (2315mg/kg)   Journal of the American Oil Chemists' Society. Vol. 37, Pg. 40, 1960.

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