Cas no 80286-58-4 (Artemisic acid)

Artemisic acid is a sesquiterpene compound derived from Artemisia annua, serving as a key intermediate in the biosynthesis of artemisinin, a potent antimalarial agent. Its structural features include a carboxylic acid functional group and a sesquiterpene backbone, enabling further chemical modifications for pharmaceutical applications. Artemisic acid is valued for its role in semi-synthetic artemisinin production, offering a scalable and cost-effective alternative to plant extraction. Its high purity and stability make it suitable for research and industrial use in antimalarial drug development. Additionally, it serves as a precursor for other bioactive terpenoids, underscoring its versatility in medicinal chemistry and synthetic biology applications.
Artemisic acid structure
Artemisic acid structure
Product Name:Artemisic acid
CAS No:80286-58-4
MF:C15H22O2
MW:234.333984851837
CID:722316
PubChem ID:10922465
Update Time:2025-06-08

Artemisic acid Chemical and Physical Properties

Names and Identifiers

    • Artemisinic acid
    • 2-[(1R,4R,4aS,8aR)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]prop-2-enoic acid
    • 1-Naphthaleneaceticacid, 1,2,3,4,4a,5,6,8a-octahydro-4,7-dimethyl-a-methylene-, (1R,4R,4aS,8aR)-
    • Artimisinic Acid
    • Arteannuic acid
    • Artemisic acid
    • Qing Hao acid
    • Qing Hau acid
    • [ "4", "11(13)-Cadinadien-12-oic acid" ]
    • (+)-artemisinic acid
    • 53N99527G7
    • 2-((1R,4R,4aS,8aR)-4,7-Dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)prop-2-enoic acid
    • Artemisinic-acid
    • PLQMEXSCSAIXGB-SAXRGWBVSA-N
    • BCP12768
    • W2206
    • C20309
    • 222F86B0-6F
    • s9135
    • (1R,4R,4aS,8aR)-1,2,3,4,4a,5,6,8a-Octahydro-4,7-dimethyl-α-methylene-1-naphthaleneacetic acid (ACI)
    • 1-Naphthaleneacetic acid, 1,2,3,4,4a,5,6,8a-octahydro-4,7-dimethyl-α-methylene-, [1R-(1α,4β,4aβ,8aβ)]- (ZCI)
    • Arteannuinic acid
    • Artemisininic acid
    • NS00002666
    • DTXSID301001147
    • 2-(4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)prop-2-enoic acid
    • AKOS017343176
    • 1ST14288
    • SINGLEEX ARTEMISINIC ACID
    • A856098
    • 4,11(13)-Cadinadien-12-oic acid;Artemisic acid
    • CCG-266821
    • 1-NAPHTHALENEACETIC ACID, 1,2,3,4,4A,5,6,8A-OCTAHYDRO-4,7-DIMETHYL-.ALPHA.-METHYLENE-, (1R,4R,4AS,8AR)-
    • 80286-58-4
    • Qing Hao acid; Artemisinic acid; Arteannuic acid
    • 2-((1r,4r,4as,8ar)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)acrylic acid
    • 222F86B0-6F56-4D85-98B2-F1B0E146A747
    • CHEMBL457385
    • MFCD00238540
    • SCHEMBL159983
    • Q27132774
    • EC 617-040-5
    • ARTEMISINIC ACID [INCI]
    • 1-Naphthaleneacetic acid, 1,2,3,4,4a,5,6,8a-octahydro-4,7-dimethyl-alpha-methylene-, (1R-(1alpha,4beta,4abeta,8abeta))-
    • CS-0018305
    • UNII-53N99527G7
    • AC-34595
    • LMPR0103190015
    • 4,11(13)-Cadinadien-12-oic acid
    • HY-N1984
    • AS-78501
    • 1-NAPHTHALENEACETIC ACID, 1,2,3,4,4A,5,6,8A-OCTAHYDRO-4,7-DIMETHYL-.ALPHA.-METHYLENE-, (1R-(1.ALPHA.,4.BETA.,4A.BETA.,8A.BETA.))-
    • Artemisinicacid
    • 4,11(13)-Amorphadien-12-oic acid
    • 2-[(1R,4R,4aS,8aR)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]prop-2-enoicacid
    • CHEBI:63749
    • Artemisinic acid(+)-artemisinic acid; Arteannuic acid; 2-[(1R,4R,4aS,8aR)-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,4R,4AS,8AR)-
    • 2-(4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphtalen-1-yl)prop-2-enoic acid
    • DA-61227
    • 2-((4R)-4,7-Dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)prop-2-enoate
    • 2-[(4R)-4,7-Dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]prop-2-enoate
    • MDL： N/A
    • Inchi： 1S/C15H22O2/c1-9-4-6-12-10(2)5-7-13(14(12)8-9)11(3)15(16)17/h8,10,12-14H,3-7H2,1-2H3,(H,16,17)/t10-,12+,13+,14+/m1/s1
    • InChI Key： PLQMEXSCSAIXGB-SAXRGWBVSA-N
    • SMILES： C([C@@H]1CC[C@@H](C)[C@@H]2CCC(=C[C@H]12)C)(=C)C(=O)O

Computed Properties

  • Exact Mass: 234.16200
  • Monoisotopic Mass: 234.161979940 g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 2
  • Complexity: 367
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 4
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 37.3
  • Molecular Weight: 234.33
  • XLogP3: 3.8

Experimental Properties

  • Color/Form: Colorless crystal
  • Density: 1.019
  • Melting Point: 129-131 oC
  • Boiling Point: 373.6℃/760mmHg
  • Flash Point: 273.3°C
  • Refractive Index: 1.504
  • PSA: 37.30000
  • LogP: 3.64580
  • Solubility: Soluble in methanol, ethanol, DMSO and other organic solvents, soluble in chloroform, slightly soluble in sodium bicarbonate aqueous solution

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Artemisic acid Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Oxygen Catalysts: 2,2′-Bipyridine ,  4-(Dimethylamino)pyridine ,  Tempo ,  Copper bromide (CuBr) Solvents: Acetonitrile ;  1 h, 23 °C
1.2 Reagents: 2-Methyl-2-butene ,  Monosodium phosphate ,  Sodium chlorite Solvents: tert-Butanol ;  23 °C; 23 h, 23 °C
1.3 Reagents: Sodium sulfite Solvents: Water ;  5 min, 23 °C
Reference
Site-Selective Functionalization of Unactivated Allylic C-H Bonds via Direct Deprotonation with KTMP: Application to the Formal Total Synthesis of (+)-Artemisinin from Amorphadiene
Clanton, Nicholas A. ; et al, Organic Letters, 2023, 25(1), 277-281

Production Method 2

Reaction Conditions
1.1 Reagents: Sodium bicarbonate ,  Dess-Martin periodinane Solvents: Dichloromethane ;  3 h, 0 °C
1.2 Reagents: Sodium thiosulfate Solvents: Water
1.3 Reagents: 2-Methyl-2-butene ,  Monosodium phosphate ,  Sodium chlorite Solvents: tert-Butanol ,  Water ;  25 °C; 2 h, 25 °C
Reference
An enantioselective ambimodal cross-Diels-Alder reaction and applications in synthesis
Xu, Meng-Meng; et al, Nature Catalysis, 2021, 4(10), 892-900

Production Method 3

Reaction Conditions
1.1 Reagents: Potassium hydroxide
Reference
Biosynthesis of arteannuin. II. Chemical synthesis of the precursors [15-2H]- and [15-3H]-arteannuic acid
Xia, Zhiqiang; et al, Huaxue Xuebao, 1991, 49(12), 1514-17

Production Method 4

Reaction Conditions
1.1 -
2.1 Reagents: Potassium hydroxide ,  Borate(1-), tetrahydro-t4-, sodium
Reference
Biosynthesis of arteannuin. II. Chemical synthesis of the precursors [15-2H]- and [15-3H]-arteannuic acid
Xia, Zhiqiang; et al, Huaxue Xuebao, 1991, 49(12), 1514-17

Production Method 5

Reaction Conditions
1.1 Reagents: Lithium bromide Solvents: Tetrahydrofuran ;  -78 °C; 1 h, -78 °C; -78 °C → 25 °C; overnight, 25 °C
1.2 Reagents: Lithium iodide ;  48 h, 25 °C
1.3 Reagents: Ammonium chloride Solvents: Water ;  0 °C
2.1 Reagents: Sodium bicarbonate ,  Dess-Martin periodinane Solvents: Dichloromethane ;  3 h, 0 °C
2.2 Reagents: Sodium thiosulfate Solvents: Water
2.3 Reagents: 2-Methyl-2-butene ,  Monosodium phosphate ,  Sodium chlorite Solvents: tert-Butanol ,  Water ;  25 °C; 2 h, 25 °C
Reference
An enantioselective ambimodal cross-Diels-Alder reaction and applications in synthesis
Xu, Meng-Meng; et al, Nature Catalysis, 2021, 4(10), 892-900

Production Method 6

Reaction Conditions
1.1 Reagents: Oxygen ,  Hydrazine hydrate (1:1) Solvents: 1-Propanol ;  25 min, 100 °C
Reference
Continuous Flow Reduction of Artemisinic Acid Utilizing Multi-Injection Strategies-Closing the Gap Towards a Fully Continuous Synthesis of Antimalarial Drugs
Pieber, Bartholomaeus; et al, Chemistry - A European Journal, 2015, 21(11), 4368-4376

Production Method 7

Reaction Conditions
1.1 Reagents: 2-Methyl-2-butene ,  Monosodium phosphate ,  Sodium chlorite Solvents: tert-Butanol ,  Water ;  25 °C; 2 h, 25 °C
Reference
An enantioselective ambimodal cross-Diels-Alder reaction and applications in synthesis
Xu, Meng-Meng; et al, Nature Catalysis, 2021, 4(10), 892-900

Production Method 8

Reaction Conditions
1.1 Reagents: Potassium hydroxide ,  Borate(1-), tetrahydro-t4-, sodium
Reference
Biosynthesis of arteannuin. II. Chemical synthesis of the precursors [15-2H]- and [15-3H]-arteannuic acid
Xia, Zhiqiang; et al, Huaxue Xuebao, 1991, 49(12), 1514-17

Production Method 9

Reaction Conditions
1.1 Solvents: Water ;  120 h, 30 °C
Reference
Production of the antimalarial drug precursor artemisinic acid in engineered yeast
Ro, Dae-Kyun; et al, Nature (London, 2006, 440(7086), 940-943

Production Method 10

Reaction Conditions
1.1 Catalysts: Cytochrome P450 Solvents: Water
Reference
A chicory cytochrome P450 mono-oxygenase CYP71AV8 for the oxidation of (+)-valencene
Cankar, Katarina; et al, FEBS Letters, 2011, 585(1), 178-182

Production Method 11

Reaction Conditions
1.1 Reagents: Butyllithium ,  Potassium tert-butoxide Solvents: Tetrahydrofuran ,  Hexane ;  -78 °C; 15 min, -78 °C
1.2 Reagents: 2,2,6,6-Tetramethylpiperidine ;  -78 °C; 15 min, -78 °C
1.3 1 h, -78 °C
1.4 Reagents: Triisopropyl borate ;  30 min, -78 °C → rt
1.5 Reagents: Hydrogen peroxide Solvents: Water ;  < 30 °C; 30 min, < 30 °C
2.1 Reagents: Oxygen Catalysts: 2,2′-Bipyridine ,  4-(Dimethylamino)pyridine ,  Tempo ,  Copper bromide (CuBr) Solvents: Acetonitrile ;  1 h, 23 °C
2.2 Reagents: 2-Methyl-2-butene ,  Monosodium phosphate ,  Sodium chlorite Solvents: tert-Butanol ;  23 °C; 23 h, 23 °C
2.3 Reagents: Sodium sulfite Solvents: Water ;  5 min, 23 °C
Reference
Site-Selective Functionalization of Unactivated Allylic C-H Bonds via Direct Deprotonation with KTMP: Application to the Formal Total Synthesis of (+)-Artemisinin from Amorphadiene
Clanton, Nicholas A. ; et al, Organic Letters, 2023, 25(1), 277-281

Production Method 12

Reaction Conditions
1.1 Reagents: Sodium hydroxide Solvents: Water ;  overnight, 60 °C
1.2 Reagents: Oxalyl chloride Solvents: Dimethylformamide ,  Dichloromethane ;  0 °C; 1 h, 0 °C; 0 °C → 25 °C; 4 h, 25 °C
1.3 Reagents: Lithium bromide Solvents: Tetrahydrofuran ;  -78 °C; 1 h, -78 °C; -78 °C → 25 °C; overnight, 25 °C
1.4 Reagents: Lithium iodide ;  48 h, 25 °C
1.5 Reagents: Ammonium chloride Solvents: Water ;  0 °C
2.1 Reagents: Sodium bicarbonate ,  Dess-Martin periodinane Solvents: Dichloromethane ;  3 h, 0 °C
2.2 Reagents: Sodium thiosulfate Solvents: Water
2.3 Reagents: 2-Methyl-2-butene ,  Monosodium phosphate ,  Sodium chlorite Solvents: tert-Butanol ,  Water ;  25 °C; 2 h, 25 °C
Reference
An enantioselective ambimodal cross-Diels-Alder reaction and applications in synthesis
Xu, Meng-Meng; et al, Nature Catalysis, 2021, 4(10), 892-900

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