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
 
Notes:
isolated from artemisia annua.
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2-[(4R)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]prop-2-enoic acid (Click)
CAS Number: 80286-58-4Picture of molecule
FDA UNII: 53N99527G7
XlogP3-AA: 3.80 (est)
Molecular Weight: 234.33874000
Formula: C15 H22 O2
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: cosmetic ingredient for skin conditioning
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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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)
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Organoleptic Properties:
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: skin conditioning
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Suppliers:
BOC Sciences
For experimental / research use only.
Artemisic Acid
Carbosynth
For experimental / research use only.
Artemisic Acid
Coompo
For experimental / research use only.
Artemisic Acid from Plants ≥96%
Odor: characteristic
Use: Shows antibacterial activity. Artemisinic acid, isolated as the active principles of the medicinal plant Artemisia annua L., Artemisinic acid is a major precursor of artemisinin (an antimalaric compound), isolated as the active principles of the medicinal plant Artemisia annua L. Although total synthesis of artemisinin is difficult and costly, the semi-synthesis of artemisinin or any derivative from microbially sourced artemisinic acid, its immediate precursor, could be a cost-effective, environmentally friendly, high-quality and reliable source of artemisinin.
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
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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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 124033
National Institute of Allergy and Infectious Diseases: Data
 2-[(4R)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]prop-2-enoic acid
Chemidplus: 0080286584
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References:
 2-[(4R)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]prop-2-enoic acid
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 124033
Pubchem (sid): 135079432
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
Golm Metabolome Database: Search
KEGG (GenomeNet): C20309
HMDB (The Human Metabolome Database): Search
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 artemisia annva
Search Trop  Picture
 wormwood wild wormwood
Search Trop  Picture
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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
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Articles:
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].
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