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
• Article Data: 7

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

General Description

Hemigossypol are chemicals found in cottonseed that have been identified as potential toxins. They have been shown to have anti-fertility effects in both males and females by interfering with sperm production and maturation in males and disrupting ovarian function in females. Hemigossypol has also been linked to reproductive abnormalities and reduced reproductive performance in livestock animals. Additionally, it has been implicated in liver damage and potentially carcinogenic effects. Due to these harmful effects, efforts are being made to develop strategies to reduce the levels of hemigossypol in cottonseed products to minimize the risk of toxicity in animals and humans.

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

• 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 
• 499-75-2 carvacrol 
• 1665-99-2 2-hydroxy-6-isopropyl-3-methyl-benzaldehyde 

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.

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.

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