Cited by 17Plant biochemistry and biosynthesisSesquiterpenes and Asteraceae StudiesMolecular spectroscopy and chirality

Photo-oxygenation of Phytol and the Structure Revision of Phytene-1,2-diol from Artemisia annua to Phytene-1-ol-2-Hydroperoxidek

Wong, Ho-Fai, Brown, Geoffrey D.·2002·Journal of Chemical Research

Abstract

Photo-oxygenation of racemic phytol has yielded two secondary allylic hydroperoxides and an endoperoxide hemi-acetal, 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.

Integrity signals

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Crossref · 10.3184/030823402103170376

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11 of 11 references verified0 citation errors · 0 not checkable

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  • The diterpene phytene-1-ol-2-hydroperoxide (553) was wrongly assigned as phytene-1,2-diol (552) when first described as a natural product from A. annua.

    “The structure of the diterpene phytene-1-ol-2-hydroperoxide (553) [9,260] was wrongly assigned as phytene-1,2-diol (552), when it was first described as a natural product from A. annua [261].”
  • Photo-oxygenation of commercially available phytol produced both phytene-1,2-diol (552) in racemic form and its 2-hydroperoxy analogue (553).

    “Structural revision was made on the basis of studies of the photo-oxygenation of commercially-available phytol, which produced both phytene-1,2-diol (552) (in racemic form), as well as its 2-hydroperoxy analogue (553) [260].”

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Authors
Wong, H.-F., & Brown, G. D.
Affiliations
University of Hong Kong (HK)
Corresponding author
Brown, Geoffrey D.
Venue
Journal of Chemical Research
Published
2002-01
Volume
2002
Issue
1
Pages
30-33
ISSN
  • 1747-5198 (ISSN-L)
  • 2047-6507
OpenAlex
W2949505503
Cited by
17
References
11
Citations by year
2026: 1 · 2025: 1 · 2024: 1 · 2022: 1 · 2021: 1 · 2020: 1 · 2018: 1 · 2015: 2
FWCI
0.46
Type
journal article
Language
en
Open access
closed
Locations
Journal of Chemical Research (publishedVersion)
Topics
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Plant biochemistry and biosynthesis
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Cancer Research › Sesquiterpenes and Asteraceae Studies
  • Physical Sciences › Chemistry › Spectroscopy › Molecular spectroscopy and chirality
Keywords
phytol, photooxygenation, singlet oxygen, allylic hydroperoxides, Artemisia annua, structure revision, diastereomers, spectral properties, carotenoids

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