97763-23-0

Basic information

• Product Name: 3-hydroxy-2-methyl-5-[(2R)-6-methylhept-5-en-2-yl]cyclohexa-2,5-diene-1,4-dione
• Synonyms: 2,5-Cyclohexadiene-1,4-dione, 5-[(1R)-1,5-dimethyl-4-hexen-1-yl]-3-hydroxy-2-methyl-
• CAS NO: 97763-23-0
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.3175
• Mol File: 97763-23-0.mol

Chemical Properties

• Boiling Point: 359.3°C at 760 mmHg
• Flash Point: 185.3°C
• Density: 1.103g/cm³
• Vapor Pressure: 1.31E-06mmHg at 25°C
• Refractive Index: 1.537
• PKA: 3.29±0.50(Predicted)
• CAS DataBase Reference: 3-hydroxy-2-methyl-5-[(2R)-6-methylhept-5-en-2-yl]cyclohexa-2,5-diene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxy-2-methyl-5-[(2R)-6-methylhept-5-en-2-yl]cyclohexa-2,5-diene-1,4-dione(97763-23-0)
• EPA Substance Registry System: 3-hydroxy-2-methyl-5-[(2R)-6-methylhept-5-en-2-yl]cyclohexa-2,5-diene-1,4-dione(97763-23-0)

Safety Data

• Hazardous Substances Data: 97763-23-0(Hazardous Substances Data)

Upstream product

• 3600-95-1 (-)-perezone 
• 2055-46-1 2-mercapto-3,4,5,6-tetrahydropyrimidine 
• 67-56-1 methanol 
• 13120-66-6 2-(1,5-dimethyl-4-hexenyl)-3-hydroxy-5-methyl-1,4-benzoquinone 

Downstream Products

• 10124-08-0 perezinone 

Relevant articles and documents

Green Production of Indolylquinones, Derivatives of Perezone, and Related Molecules, Promising Antineoplastic Compounds

A green approach to produce the indolyl derivatives from four natural quinones (perezone, isoperezone, menadione, and plumbagin) was performed; in this regard, a comparative study was accomplished among the typical mantle heating and three nonconventional

Detailed Studies of Perezone Rearrangements

The isomerization of perezone (1) into isoperezone (2) by means of 3,4,5,6-tetrahydro-2-pyrimidinethiol afforded 6-methoxyperezone (6), the sulfide 7, and the heterocycle 8 as by-products. Addition of a small amount of water to the reaction system increased the yield of 2 from 45 to 65%. The pathway for the formation of 6, 7, and 8 is discussed. The reaction of 2 with silica gel or with p-TsOH regioselectively yielded β-isopipitzol (3) or dihydroisoperezinone (4) in 72 and 82% yield, respectively.

Synthesis, cytotoxic and antioxidant evaluations of amino derivatives from perezone

A series of eight amino derivatives (3a-h) from perezone 1 were prepared by nucleophilic addition of bioactive amines v.gr. melatonin, acetyl tryptamine, tryptophan and other amino acids esters (valine, leucine and methionine). Their structures were elucidated by spectroscopy data. The cytotoxic evaluation against four human tumor cell lines PC-3, K-562, HCT-15 and SKLU-1 was performed as well as the TBARS assay for antioxidant activity. The results suggest that 1 and its isomer 4 were highly active against all cell lines, 4 was twice as potent than 1 against PC-3 and HCT-15. The derivative 3a (IC50 = 7.5 ± 0.3 μM) was more active than 1 against HCT-15 whereas 3h was selective against K-562 with IC50 = 4.5 ± 0.4 μM. The TBARS assay has shown that 3c with IC50 = 5.564 ± 0.24 μM is a potent antioxidant with superior effect comparing to α-tocopherol and moreover was more active than the precursor molecule 1.