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Dihydroartemisinic acid

$192

  • Brand : BIOFRON

  • Catalogue Number : BD-D1097

  • Specification : HPLC≥98%

  • CAS number : 85031-59-0

  • Formula : C15H24O2

  • Molecular Weight : 236.355

  • PUBCHEM ID : 11020893

  • Volume : 20mg

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Catalogue Number

BD-D1097

Analysis Method

HPLC,NMR,MS

Specification

HPLC≥98%

Storage

-20℃

Molecular Weight

236.355

Appearance

Powder

Botanical Source

Artemisia annua

Structure Type

Sesquiterpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1CCC(C2C1CCC(=C2)C)C(C)C(=O)O

Synonyms

dihydroartemisininic acid/dihydroartemisinic acid/dihydroqinghao acid/Dihydroartemisinic acid/(2R)-dihydroartemisinic acid/DHAA

IUPAC Name

(2R)-2-[(1R,4R,4aS,8aS)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]propanoic acid

Applications

Dihydroartemisinic acid (Dihydroqinghao acid), isolated as a natural product from Artemisia annua, is a biosynthetic precursor to the antimalarial agent Artemisinin[1].

Density

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

Boiling Point

Melting Point

InChl

InChI=1S/C15H24O2/c1-9-4-6-12-10(2)5-7-13(14(12)8-9)11(3)15(16)17/h8,10-14H,4-7H2,1-3H3,(H,16,17)/t10-,11-,12+,13+,14+/m1/s1

InChl Key

JYGAZEJXUVDYHI-DGTMBMJNSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:85031-59-0) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

21030913

Abstract

The Chinese medicinal plant Artemisia annua L. (Qinghao) is the only known source of the sesquiterpene artemisinin (Qinghaosu), which is used in the treatment of malaria. Artemisinin is a highly oxygenated sesquiterpene, containing a unique 1,2,4-trioxane ring structure, which is responsible for the antimalarial activity of this natural product. The phytochemistry of A. annua is dominated by both sesquiterpenoids and flavonoids, as is the case for many other plants in the Asteraceae family. However, A. annua is distinguished from the other members of the family both by the very large number of natural products which have been characterised to date (almost six hundred in total, including around fifty amorphane and cadinane sesquiterpenes), and by the highly oxygenated nature of many of the terpenoidal secondary metabolites. In addition, this species also contains an unusually large number of terpene allylic hydroperoxides and endoperoxides. This observation forms the basis of a proposal that the biogenesis of many of the highly oxygenated terpene metabolites from A. annua – including artemisinin itself – may proceed by spontaneous oxidation reactions of terpene precursors, which involve these highly reactive allyllic hydroperoxides as intermediates. Although several studies of the biosynthesis of artemisinin have been reported in the literature from the 1980s and early 1990s, the collective results from these studies were rather confusing because they implied that an unfeasibly large number of different sesquiterpenes could all function as direct precursors to artemisinin (and some of the experiments also appeared to contradict one another). As a result, the complete biosynthetic pathway to artemisinin could not be stated conclusively at the time. Fortunately, studies which have been published in the last decade are now providing a clearer picture of the biosynthetic pathways in A. annua. By synthesising some of the sesquiterpene natural products which have been proposed as biogenetic precursors to artemisinin in such a way that they incorporate a stable isotopic label, and then feeding these precursors to intact A. annua plants, it has now been possible to demonstrate that dihydroartemisinic acid is a late-stage precursor to artemisinin and that the closely related secondary metabolite, artemisinic acid, is not (this approach differs from all the previous studies, which used radio-isotopically labelled precursors that were fed to a plant homogenate or a cell-free preparation). Quite remarkably, feeding experiments with labeled dihydroartemisinic acid and artemisinic acid have resulted in incorporation of label into roughly half of all the amorphane and cadinane sesquiterpenes which were already known from phytochemical studies of A. annua. These findings strongly support the hypothesis that many of the highly oxygenated sesquiterpenoids from this species arise by oxidation reactions involving allylic hydroperoxides, which seem to be such a defining feature of the chemistry of A. annua. In the particular case of artemisinin, these in vivo results are also supported by in vitro studies, demonstrating explicitly that the biosynthesis of artemisinin proceeds via the tertiary allylic hydroperoxide, which is derived from oxidation of dihydroartemisinic acid. There is some evidence that the autoxidation of dihydroartemisinic acid to this tertiary allylic hydroperoxide is a non-enzymatic process within the plant, requiring only the presence of light; and, furthermore, that the series of spontaneous rearrangement reactions which then convert this allylic hydroperoxide to the 1,2,4-trioxane ring of artemisinin are also non-enzymatic in nature.

KEYWORDS

artemisinin, dihydroartemisinic acid, sesquiterpene, biosynthesis, Artemisia annua, phytochemistry, oxidation, allylic hydroperoxide

Title

The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao)

Author

Geoffrey D. Brown

Publish date

2010 Nov;