Name: GOSSYPOL
SKU: 303-45-7

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Basic Information

Molecular Structure:
CAS No.:	303-45-7
Name:	GOSSYPOL

Formula:	C₃₀H₃₀O₈
Molecular Weight:	518.563
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;
EINECS:	636-899-7
Density:	1.403 g/cm³
Melting Point:	181-183 °C
Boiling Point:	707.888 °C at 760 mmHg
Flash Point:	395.872 °C
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.
Hazard Symbols:	Xi, Xn
Risk Codes:	22-40-36/37/38
Safety:	22-36-36/37/39-27-26
PSA:	155.52000
LogP:	6.38220

Synthetic route

: 5453-04-3, 866541-93-7, 1189561-66-7
(±)-gossypol acetic acid

: 303-45-7
(rac)-gossypol

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With hydroquinone at 180℃; under 5 - 15 Torr; for 2.5h;	72%

: 784206-41-3
apogossypol

: 303-45-7
(rac)-gossypol

Conditions

Conditions	Yield
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

Conditions	Yield
In water; acetone for 48h;

: 17273-29-9, 38152-98-6, 125278-11-7
Gossypol

: 303-45-7
(rac)-gossypol

Conditions

Conditions	Yield
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

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

: C54H54N4O10

: 303-45-7
(rac)-gossypol

Conditions

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

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

: 303-45-7
(rac)-gossypol

Conditions

Conditions	Yield
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

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Consensus Reports

EPA Genetic Toxicology Program.

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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Consensus Reports

Specification