1564-99-4

Basic information

• Product Name: 3,7-dimethyloct-5-ene-1,7-diol
• Synonyms: 3,7-Dimethyloct-5-ene-1,7-diol; 5-octene-1,7-diol, 3,7-dimethyl-
• CAS NO: 1564-99-4
• Molecular Formula: C₁₀H₂₀O₂
• Molecular Weight: 172.26
• Mol File: 1564-99-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 279.9°C at 760 mmHg
• Flash Point: 126.9°C
• Density: 0.943g/cm³
• Vapor Pressure: 0.00047mmHg at 25°C
• Refractive Index: 1.475
• CAS DataBase Reference: 3,7-dimethyloct-5-ene-1,7-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 3,7-dimethyloct-5-ene-1,7-diol(1564-99-4)
• EPA Substance Registry System: 3,7-dimethyloct-5-ene-1,7-diol(1564-99-4)

Safety Data

• Hazardous Substances Data: 1564-99-4(Hazardous Substances Data)

Upstream product

• 106-22-9 Citronellol 
• 1147880-35-0 (R)-citronallol acetate oxide 
• 1117-61-9 (3R)-citronellol 

Relevant articles and documents

Dark singlet oxygenation of β-citronellol: A key step in the manufacture of rose oxide

We describe the development of a scalable process for the "dark" singlet oxygenation of β-citronellol as a key step in the manufacture of the fragrance compound, rose oxide. This process, based on catalytic disproportionation of hydrogen peroxide into singlet oxygen and water, has been carried out on production scale in 10 m3 reactors.

Unusual Oxidative Dealkylation Strategy toward Functionalized Phenalenones as Singlet Oxygen Photosensitizers and Photophysical Studies

A series of functionalized 6-alkoxy phenalenones was prepared through an unprecedented oxidative dealkylation of readily available phenalene precursors. The starting phenalenes were efficiently synthesized via an aminocatalyzed annulation/O-alkylation str

A biocatalytic route towards rose oxide using chloroperoxidase

The chiral monoterpene alcohol citronellol was converted to the corresponding bromohydrin by the haem-thiolate enzyme chloroperoxidase (CPO) from Caldariomyces fumago in the presence of hydrogen peroxide and bromide ions. A conversion rate of 51% could be achieved under adapted reaction conditions, which easily yield product in the gramme per litre range while only needing catalytic amounts of enzyme. The bromohydroxylation was shown to be highly regioselective yielding 6-bromo-3,7-dimethyloctane-1,7-diol as the sole product. Product identity was confirmed by GC-MS, 1H- and 13C-NMR spectroscopy and the synthesis of reference compounds. However, the reaction was shown to be non-stereospecific because enantiopure (R)- and (S)-citronellol, respectively, gave 1:1-diasteromeric mixtures of the corresponding bromohydrins. A racemic mixture of (R/S)-citronellol was bromohydroxylated without any detectable enantiodiscrimination. The total lack of stereospecificity and enantiodiscrimination points to a reaction mechanism where the oxidised bromide intermediate is not a ligand to the Fe(III)-haem at the distal site but is released from the enzyme active site. The final bromide transfer occurs probably outside the active site via a diffusible oxidised bromide species and the demonstrated regioselectivity is purely chemically controlled. The generated bromohydrins can be straightforward converted via two reactions steps into rose oxide which is a highly valuable flavour and fragrance substance.