438536-34-6

Basic information

• Product Name: 3(20)-Phytene-1,2-diol
• Synonyms: 3(20)-Phytene-1,2-diol;3-Methylidene-7,11,15-trimethylhexadecan-1,2-diol
• CAS NO: 438536-34-6
• Molecular Formula: C20H40O2
• Molecular Weight: 312.5304
• Mol File: 438536-34-6.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3(20)-Phytene-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 3(20)-Phytene-1,2-diol(438536-34-6)
• EPA Substance Registry System: 3(20)-Phytene-1,2-diol(438536-34-6)

Safety Data

• Hazardous Substances Data: 438536-34-6(Hazardous Substances Data)

Upstream product

• 253686-88-3 (E)-3,7,11,15-tetramethylhexadec-2-en-1-ol 
• 7541-49-3 3,7,11,15-tetramethyl-2-hexadecen-1-ol 
• 107438-44-8 [3-methyl-3-(4,8,12-trimethyl-tridecyl)-oxiranyl]-methanol 
• 100605-81-0 2-hydroperoxy-7,11,15-trimethyl-3-methylenehexadecan-1-ol 

Relevant articles and documents

Selective C-H Allylic Oxygenation of Cycloalkenes and Terpenoids Photosensitized by [Cu(Xantphos)(neoc)]BF4

We present herein for the first time the use of the [Cu(Xantphos)(neoc)]BF4 as a photocatalyst for the selective C-H allylic oxygenation of cycloalkenes into the corresponding allylic hydroperoxides or alcohols in the presence of molecular oxygen. The proposed methodology affords the products at good yields and has also been applied successfully to several bioactive terpenoids, such as geraniol, linalool, β-citronellol, and phytol. A mechanistic study involving also kinetic isotope effects (KIEs) supports the proposed singlet oxygen-mediated reaction. On the basis of the high chemoselectivity and yields and the fast and clean reaction processes observed, the present catalytic system, [Cu(Xantphos)(neoc)]BF4, has also been applied to the synthesis, at a laboratory scale, of the cis-Rose oxide, a well-known perfumery ingredient used in rose and geranium perfumes.

Photo-oxygenation of phytol and the structure revision of phytene-1,2-diol from Artemisia annua to phytene-1-ol-2-hydroperoxide

Photo-oxygenation of racemic phytol has yielded two secondary allylic hydroperoxides and an endoperoxide hemiacetal, which are the expected products from the "ene-type" reaction of singlet oxygen with the tri-substituted double bond in phytol. Spectral properties for one of the diastereoisomers of phytene-1-ol-2-hydroperoxide obtained from synthesis are shown to be identical with those of a natural product previously reported from Artemisia annua, which, it is concluded, was wrongly assigned as phytene-1,2-diol.