Photo-oxygenation of Phytol and the Structure Revision of Phytene-1,2-diol from Artemisia annua to Phytene-1-ol-2-Hydroperoxidek
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.
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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].”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [260]
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].”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [260]
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- Authors
- Wong, H.-F., & Brown, G. D.
- Affiliations
- University of Hong Kong (HK)
- Corresponding author
- Brown, Geoffrey D.
- ORCID
- Brown, Geoffrey D.
- Venue
- Journal of Chemical Research
- Publisher
- SAGE Publications
- 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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