artemisic acid
(1R-(1alpha,4beta,4abeta,8abeta))-1,2,3,4,4a,5,6,8a-octahydro-4,7-dimethyl-alpha-methylene-1-naphthalene acetic acid
Identification
| Name | artemisic acid |
| IUPAC | 2-[(4R)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]prop-2-enoic acid |
| CAS Number | 80286-58-4 |
| FDA UNII | 53N99527G7 |
| Molecular Formula | C15 H22 O2 |
| Molecular Weight | 234.33874000 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 373.00 to 374.00 °C. @ 760.00 mm Hg (est) |
| Flash Point | 524.00 °F. TCC ( 273.30 °C. ) (est) |
| logP (o/w) | 5.086 (est) |
| Soluble in | water, 3.631 mg/L @ 25 °C (est) |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | skin conditioning |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | cosmetic ingredient for skin conditioning |
| Recommendation for artemisic acid usage levels up to | not for fragrance use. |
| Recommendation for artemisic acid flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
artemisinic acid
2-[(4R)-4,7-
dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]prop-2-enoic acid
1-
naphthaleneacetic acid, 1,2,3,4,4a,5,6,8a-octahydro-4,7-dimethyl-alpha-methylene-, (1R-(1alpha,4beta,4abeta,8abeta))-
(1R-(1alpha,4beta,4abeta,8abeta))-1,2,3,4,4a,5,6,8a-
octahydro-4,7-dimethyl-alpha-methylene-1-naphthalene acetic acid
PubMed:
Kinetic analysis of cytochrome P450 reductase from Artemisia annua reveals accelerated rates of NADH-dependent flavin reduction.
PubMed:
A rapid method for the determination of artemisinin and its biosynthetic precursors in Artemisia annua L. crude extracts.
PubMed:
[Variation of content of artemisic acid in different growth stages of Artemisia annua].
PubMed:
Preparation and application of reversed phase Chromatorotor for the isolation of natural products by centrifugal preparative chromatography.
PubMed:
The metabolite chemotype of Nicotiana benthamiana transiently expressing artemisinin biosynthetic pathway genes is a function of CYP71AV1 type and relative gene dosage.
PubMed:
High-level semi-synthetic production of the potent antimalarial artemisinin.
PubMed:
A continuous-flow process for the synthesis of artemisinin.
PubMed:
Malaria drug made in yeast causes market ferment.
PubMed:
Hydroxyl octadecenoic acids biosynthesized by crown galls of Panax quinquefolium induced by artermisinic acid.
PubMed:
Artemisinic acid inhibits melanogenesis through downregulation of C/EBP α-dependent expression of HMG-CoA reductase gene.
PubMed:
Characterization of cytochrome P450 monooxygenases isolated from trichome enriched fraction of Artemisia annua L. leaf.
PubMed:
Infectious diseases. Can new chemistry make a malaria drug plentiful and cheap?
PubMed:
Artemisinic acid is a regulator of adipocyte differentiation and C/EBP δ expression.
PubMed:
Three sesquiterpene compounds biosynthesised from artemisinic acid using suspension-cultured cells of Averrhoa carambola (Oxalidaceae).
PubMed:
Chemotype-dependent metabolic response to methyl jasmonate elicitation in Artemisia annua.
PubMed:
[Biotransformation of artemisinic acid by cell suspension cultures of Cephalotaxus fortunei and Artemisia annua].
PubMed:
The production of artemisinin precursors in tobacco.
PubMed:
Demand for malaria drug soars.
PubMed:
Drying affects artemisinin, dihydroartemisinic acid, artemisinic acid, and the antioxidant capacity of Artemisia annua L. leaves.
PubMed:
Salicylic acid activates artemisinin biosynthesis in Artemisia annua L.
PubMed:
Developing an industrial artemisinic acid fermentation process to support the cost-effective production of antimalarial artemisinin-based combination therapies.
PubMed:
Induction of multiple pleiotropic drug resistance genes in yeast engineered to produce an increased level of anti-malarial drug precursor, artemisinic acid.
PubMed:
[Determination of artemisinin, arteannuin B and artemisinic acid in Herba Artemisiae Annuae by HPLC-UV-ELSD].
PubMed:
Production of artemisinin by genetically-modified microbes.
PubMed:
Metabolic fingerprinting investigation of Artemisia annua L. in different stages of development by gas chromatography and gas chromatography-mass spectrometry.
PubMed:
Engineering Escherichia coli for production of functionalized terpenoids using plant P450s.
PubMed:
Nutrient deficiency in the production of artemisinin, dihydroartemisinic acid, and artemisinic acid in Artemisia annua L.
PubMed:
Production of the antimalarial drug precursor artemisinic acid in engineered yeast.
PubMed:
Simultaneous densitometric determination of artemisinin, artemisinic acid and arteannuin-B in Artemisia annua using reversed-phase thin layer chromatography.
PubMed:
Terpenoids from the seeds of Artemisia annua.
PubMed:
Synthesis of new artemisinin analogues from artemisinic acid modified at C-3 and C-13 and their antimalarial activity.
PubMed:
Extraction of artemisinin and artemisinic acid from Artemisia annua L. using supercritical carbon dioxide.
PubMed:
Extraction of artemisinin and artemisinic acid: preparation of artemether and new analogues.
PubMed:
Crystal structure of artemisinic acid: a possible biogenetic precursor of antimalarial artemisinin from Artemisia annua.
PubMed:
[Antitumor activities of 4 derivatives of artemisic acid and artemisinin B in vitro].
PubMed:
[The constituents of young Artemisia annua].