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

CAS: 80286-58-4 C15 H22 O2 MW: 234.33874000

Identification

Nameartemisic acid
IUPAC2-[(4R)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]prop-2-enoic acid
CAS Number80286-58-4
FDA UNII53N99527G7
Molecular FormulaC15 H22 O2
Molecular Weight234.33874000

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

CosIngcosmetic data
Cosmetic Usesskin conditioning

No sensory data available

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorycosmetic ingredient for skin conditioning
Recommendation for artemisic acid usage levels up tonot for fragrance use.
Recommendation for artemisic acid flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

artemisia annva wormwood wild wormwood

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].