40817-07-0

Basic information

• Product Name: HEMIGOSSYPOL
• Synonyms: HEMIGOSSYPOL;2,3,8-Trihydroxy-6-methyl-4-isopropyl-1-naphthalenecarbaldehyde
• CAS NO: 40817-07-0
• Molecular Formula: C₁₅H₁₆O₄
• Molecular Weight: 260.29
• Mol File: 40817-07-0.mol

Chemical Properties

• Boiling Point: 470.3°C at 760 mmHg
• Flash Point: 252.4°C
• Appearance: /
• Density: 1.322g/cm³
• Vapor Pressure: 1.81E-09mmHg at 25°C
• Refractive Index: 1.693
• PKA: 8.55±0.50(Predicted)
• CAS DataBase Reference: HEMIGOSSYPOL(CAS DataBase Reference)
• NIST Chemistry Reference: HEMIGOSSYPOL(40817-07-0)
• EPA Substance Registry System: HEMIGOSSYPOL(40817-07-0)

Safety Data

• Hazardous Substances Data: 40817-07-0(Hazardous Substances Data)

Usage

Uses

Used in Research and Development:
Hemigossypol is used as a subject of research for understanding its anti-fertility effects and potential toxicity in both humans and animals. This research aims to develop strategies to reduce its levels in cottonseed products and mitigate the associated risks.
Used in Toxicology Studies:
Hemigossypol is utilized in toxicology studies to investigate its potential carcinogenic effects, liver damage, and reproductive abnormalities. These studies contribute to the understanding of the mechanisms of toxicity and help in the development of preventive measures and treatments.
Used in Agricultural and Food Industry:
Hemigossypol is used as a reference compound in the agricultural and food industry to monitor and control the levels of toxins in cottonseed products. This ensures the safety and quality of these products for consumption by animals and humans.
Used in Regulatory Frameworks:
Hemigossypol is considered in the development of regulatory frameworks and guidelines for the safe use of cottonseed products. These frameworks help in setting acceptable limits for the presence of hemigossypol in cottonseed products and enforce compliance to minimize the risk of toxicity.

InChI:InChI=1/C15H16O4/c1-7(2)12-9-4-8(3)5-11(17)13(9)10(6-16)14(18)15(12)19/h4-7,17-19H,1-3H3

Upstream product

• 57765-65-8 desoxyhemigossypol 
• 4885-02-3 Dichloromethyl methyl ether 
• 1256723-06-4 5-isopropyl-3-methyl-1,6,7-naphthalenetriol 
• 50399-96-7 4-isopropyl-2,3,8-trimethoxy-6-methyl-1-naphthaldehyde 
• 1256723-09-7 4-hydroxy-5-isopropyl-7-methylnaphtho[1,8-bc]furan-3-one 
• 1665-99-2 2-hydroxy-6-isopropyl-3-methyl-benzaldehyde 
• 499-75-2 carvacrol 

Downstream Products

• 303-45-7 (rac)-gossypol 

Relevant articles and documents

Synthesis of hemigossypol and its derivatives

Hemigossypol (3), a sesquiterpene natural product, was previously isolated from Gossypium barbadense and was shown to display improved anti-fungal activity compared to gossypol (1), the disesquiterpene dimer of hemigossypol (3). Gossypol exhibits multiple biological activities. In order to study whether hemigossypol and its derivatives retain the various bioactivities of gossypol, we developed a short and convenient synthetic scheme to synthesize hemigossypol. This is the first de novo synthesis of this natural product. In addition derivatives of hemigossypol with various 2,5-alkyl substituents were synthesized. Modification of the synthetic scheme also afforded the natural product hemigossylic lactone (4) and its 2,5-substituted derivatives.

Synthetic method of semi-gossypol, gossypol and analogues of semi-gossypol and gossypol

The invention discloses a synthetic method of semi-gossypol, gossypol and analogues of semi-gossypol and gossypol. According to the method, maltol containing substituents is taken as a raw material, and multi-stage reactions including coupling, rearrangement, reduction, oxidation and cyclization are carried out to synthesize semi-gossypol, gossypol and the analogues of semi-gossypol and gossypol.According to the method, the situation that gossypol is extracted from roots, stems, leaves and seeds of natural malva plant cotton is changed, and a new route for artificially synthesizing semi-gossypol, gossypol and the analogues of semi-gossypol and gossypol is created.

Cascade Claisen Rearrangement: Rapid Synthesis of Polysubstituted Salicylaldehydes and Total Syntheses of Hemigossypol and Gossypol

A cascade Claisen rearrangement of a well-organized maltol propargyl ether for the construction of polysubstituted salicylaldehydes is reported. This reaction features high atom economy (100 %), as well as catalyst-free and gram-scale conditions. Based on this novel methodology, the total synthesis of hemigossypol, gossypol, and their analogues has been realized.

Hemigossypol derivative, vergosin derivative, preparation of hemigossypol derivative and vergosin derivative and application to pesticides

The invention relates to a hemigossypol derivative, a vergosin derivative, preparation of the hemigossypol derivative and the vergosin derivative and application to preventing plant viruses, killing bacteria and killing insects. Meaning of groups in the f

Dirigent proteins from cotton (Gossypium sp.) for the atropselective synthesis of gossypol

Gossypol is a defense compound in cotton plants for protection against pests and pathogens. Gossypol biosynthesis involves the oxidative coupling of hemigossypol and results in two atropisomers owing to hindered rotation around the central binaphthyl bond

Regioselective oxidative dehydrogenation under nonenzymatic conditions: A synthetic route to gossypol

A practical and scalable route was developed for the total synthesis of gossypol to allow for the construction of dozens of gossypol derivatives. tBuO2Ac was found to be a highly efficient oxidant for the polymerization of hemigossypol through a biosynthetic process under nonenzymatic conditions to give gossypol. Hemigossypol was synthesized on a gram scale by starting from commercially available carvacrol and dimethyl succinate and using a Stobbe condensation, an electrophilic cyclization, and the Michael addition of ortho-quinone methide as key steps. A practical route was developed for the total synthesis of racemic gossypol. tBuO2Ac was found to be a highly efficient oxidant for the polymerization of hemigossypol under nonenzymatic conditions to give gossypol. Hemigossypol was synthesized on a gram scale from commercially available carvacrol and dimethyl succinate. Copyright

The Role of Free Radicals in the Decomposition of the Phytoalexin Desoxyhemigossypol

The cotton phytoalexin desoxyhemigossypol (dHG) decomposed rapidly in solution to give hemigossypol (HG).The rate of decomposition was retarded by the reducing agents ascorbic acid, reduced glutathione and cysteine, by the metal chelator diethylenetriaminepentaacetic acid, and by the enzyme catalase.However, the chelator, ethylenediaminetetraacetic acid did not reduce the rate of decomposition and the enzyme superoxide dismutase increased the rate of decomposition.Solutions of the phytoalexin desoxyhemigossypol-6-methyl ether were significantly more stable than were those of dHG.Oxygen-18 from water but not from oxygen gas was incorporated into HG during this decompositon.A hydroperoxynaphthalenone which loses hydrogen peroxide is proposed as an intermediate to explain this observation.The formation of hydrogen peroxide may be involved in the toxicity of this phytoalexin to plant pathogens such as Verticillium dahliae.