Cas no 85031-59-0 (Dihydroartemisinic acid)

Dihydroartemisinic acid structure
Dihydroartemisinic acid structure
Product Name:Dihydroartemisinic acid
CAS No:85031-59-0
MF:C15H24O2
MW:236.349864959717
MDL:MFCD16876168
CID:2073698
PubChem ID:11020893
Update Time:2024-10-26

Dihydroartemisinic acid Chemical and Physical Properties

Names and Identifiers

    • (2R)-dihydroartemisinic acid
    • 2-(4,7-dimethyl-(1alpha-H),2,3,(4beta-H),(4aalpha-H),5,6,(8aalpha-H)-octahydronaphthalen-1-yl)propionic acid
    • DHAA
    • dihydroartemisininic acid
    • dihydroqinghao acid
    • racemic DHAA
    • Dihydro-artmisinic acid
    • (alphaR,1R,4R,4aS,8aS)-1,2,3,4,4a,5,6,8a-Octahydro-alpha,4,7-trimethyl-1-naphthaleneacetic acid
    • Dihydroarteannuic acid
    • Dihydroartemisinic acid
    • dihydro artemisinic acid
    • (-)-dihydroartemisinic acid
    • JYGAZEJXUVDYHI-DGTMBMJNSA-N
    • s5237
    • (2R)-2-[(1R,4R,4aS,8aS)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]propanoic Acid
    • (2R)-2-[(1R)-4beta,7-Dimethyl-1,2,3,4,4abeta,5,6,8abeta-octahydronaphthalen-1alpha-yl]propionic acid
    • (αR,1R,4R,4aS,8aS)-1,2,3,4,4a,5,6,8a-Octahydro-α,4,7-trimethyl-1-naphthaleneacetic acid (ACI)
    • 1-Naphthaleneacetic acid, 1,2,3,4,4a,5,6,8a-octahydro-α,4,7-trimethyl-, [1R-[1α(R*),4β,4aβ,8aβ]]- (ZCI)
    • AC-34787
    • HY-N4106
    • CCG-266842
    • C76721
    • 85031-59-0
    • ZB1878
    • CHEBI:144078
    • CS-0032114
    • A917753
    • (R)-2-((1R,4R,4aS,8aS)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)propanoicacid
    • SCHEMBL1446617
    • CHEMBL5192325
    • DS-11979
    • (R)-2-((1R,4R,4aS,8aS)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)propanoic acid
    • AKOS027326558
    • MFCD16876168
    • (2R)-2-[(1R)-4beta,7-Dimethyl-1,2,3,4,4abeta,5,6,8abeta-octahydronaphthalen-1alpha-yl]propionate
    • Dihydroartemisinsaure
    • (-)-Dihydroartemisinate
    • (2R)-2-((1R)-4b,7-Dimethyl-1,2,3,4,4abeta,5,6,8abeta-octahydronaphthalen-1a-yl)propionic acid
    • Dihydroarteannuate
    • (2R)-2-[(1R)-4b,7-Dimethyl-1,2,3,4,4abeta,5,6,8abeta-octahydronaphthalen-1a-yl]propionate
    • 2-(4,7-Dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)propanoate
    • (2R)-2-((1R,4R,4aS,8aS)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)propanoic acid
    • (2R)-2-[(1R)-4b,7-Dimethyl-1,2,3,4,4abeta,5,6,8abeta-octahydronaphthalen-1a-yl]propionic acid
    • (2R)-2-((1R)-4b,7-Dimethyl-1,2,3,4,4abeta,5,6,8abeta-octahydronaphthalen-1a-yl)propionate
    • (2R)-2-((1R)-4beta,7-Dimethyl-1,2,3,4,4abeta,5,6,8abeta-octahydronaphthalen-1alpha-yl)propionate
    • (aR,1R,4R,4aS,8aS)-1,2,3,4,4a,5,6,8a-Octahydro-a,4,7-trimethyl-1-naphthaleneacetic Acid; Dihydroarteannuic Acid; Dihydroqinghao Acid; [1R-[1a(R*),4ss,4ass,8ass]]-1,2,3,4,4a,5,6,8a-Octahydro-a,4,7-trimethyl-1-naphthaleneacetic Acid;
    • DA-52541
    • MDL： MFCD16876168
    • 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
    • InChI Key： JYGAZEJXUVDYHI-DGTMBMJNSA-N
    • SMILES： [C@H]([C@@H]1CC[C@@H](C)[C@@H]2CCC(=C[C@H]12)C)(C)C(=O)O

Computed Properties

  • Exact Mass: 236.17800
  • Monoisotopic Mass: 236.177630004 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: 332
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 5
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 37.3
  • Molecular Weight: 236.35
  • XLogP3: 3.9

Experimental Properties

  • Color/Form: Powder
  • Density: 0.999±0.06 g/cm3 (20 oC 760 Torr),
  • Solubility: Almost insoluble (0.028 g/l) (25 o C),
  • PSA: 37.30000
  • LogP: 3.72570

Dihydroartemisinic acid Security Information

Dihydroartemisinic acid Pricemore >>

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Dihydroartemisinic acid Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Monosodium phosphate ,  Sodium hypochlorite Solvents: Dimethyl sulfoxide ,  Water ;  4 h, rt
1.2 Reagents: Phosphoric acid Solvents: Water ;  pH 2
Reference
A Novel Semi-biosynthetic Route for Artemisinin Production Using Engineered Substrate-Promiscuous P450BM3
Dietrich, Jeffrey A.; et al, ACS Chemical Biology, 2009, 4(4), 261-267

Production Method 2

Reaction Conditions
1.1 Reagents: Hydrogen peroxide ,  Hydrazine hydrate (1:1) Solvents: Isopropanol ,  Water ;  3.5 h, 30 - 32 °C; 6 - 7 h, 30 - 32 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 3, 25 - 30 °C
2.1 Reagents: Biphenyl ,  Lithium Solvents: 1,2-Dimethoxyethane ;  rt → 85 °C; 10 h, 80 - 85 °C; 85 °C → 5 °C
2.2 Solvents: Water ;  1 h, 0 - 5 °C; 2 h, 20 - 25 °C
2.3 Solvents: Toluene ;  30 min, 20 - 25 °C
2.4 Reagents: Hydrochloric acid Solvents: Water ;  pH 3.5 - 4
Reference
Amalgamation of Synthetic Biology and Chemistry for High-Throughput Nonconventional Synthesis of the Antimalarial Drug Artemisinin
Singh, Dharmendra; et al, Organic Process Research & Development, 2017, 21(4), 551-558

Production Method 3

Reaction Conditions
Reference
Asymmetric synthesis of dihydroartemisinic acid through intramolecular Stetter reaction
Rej, Rohan Kalyan; et al, Tetrahedron, 2016, 72(32), 4931-4937

Production Method 4

Reaction Conditions
1.1 Reagents: Sodium ,  Ammonia Solvents: Diethyl ether
2.1 Reagents: Chromium trioxide ,  Sulfuric acid Solvents: Acetone ,  Water
Reference
Total synthesis of arteannuin and deoxyarteannuin
Xu, Xingxiang; et al, Tetrahedron, 1986, 42(3), 819-28

Production Method 5

Reaction Conditions
Reference
Synergistic effect of coronatine and sorbitol on artemisinin production in cell suspension culture of Artemisia annua L. cv. Anamed
Salehi, Maryam; et al, Plant Cell, 2019, 137(3), 587-597

Production Method 6

Reaction Conditions
1.1 Reagents: Monosodium phosphate ,  Sodium hypochlorite Solvents: Dimethyl sulfoxide ,  Water ;  2 h, rt; 2 h, rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  15 h, rt
1.3 Reagents: Phosphoric acid ;  pH 2
Reference
Production of amorphadiene in yeast, and its conversion to dihydroartemisinic acid, precursor to the antimalarial agent artemisinin
Westfall, Patrick J.; et al, Proceedings of the National Academy of Sciences of the United States of America, 2012, 109(3),

Production Method 7

Reaction Conditions
Reference
Synergistic effect of coronatine and sorbitol on artemisinin production in cell suspension culture of Artemisia annua L. cv. Anamed
Salehi, Maryam; et al, Plant Cell, 2019, 137(3), 587-597

Production Method 8

Reaction Conditions
1.1 Reagents: Biphenyl ,  Lithium Solvents: 1,2-Dimethoxyethane ;  rt → 85 °C; 10 h, 80 - 85 °C; 85 °C → 5 °C
1.2 Solvents: Water ;  1 h, 0 - 5 °C; 2 h, 20 - 25 °C
1.3 Solvents: Toluene ;  30 min, 20 - 25 °C
1.4 Reagents: Hydrochloric acid Solvents: Water ;  pH 3.5 - 4
Reference
Amalgamation of Synthetic Biology and Chemistry for High-Throughput Nonconventional Synthesis of the Antimalarial Drug Artemisinin
Singh, Dharmendra; et al, Organic Process Research & Development, 2017, 21(4), 551-558

Production Method 9

Reaction Conditions
1.1 Reagents: Chromium trioxide ,  Sulfuric acid Solvents: Acetone ,  Water
Reference
Total synthesis of arteannuin and deoxyarteannuin
Xu, Xingxiang; et al, Tetrahedron, 1986, 42(3), 819-28

Production Method 10

Reaction Conditions
1.1 Reagents: Triethylamine ,  Sulfur trioxide-pyridine Solvents: Dimethyl sulfoxide ,  Dichloromethane ;  20 min, -10 °C; -10 °C → rt; 15 h, rt
2.1 Reagents: Monosodium phosphate ,  Sodium hypochlorite Solvents: Dimethyl sulfoxide ,  Water ;  4 h, rt
2.2 Reagents: Phosphoric acid Solvents: Water ;  pH 2
Reference
A Novel Semi-biosynthetic Route for Artemisinin Production Using Engineered Substrate-Promiscuous P450BM3
Dietrich, Jeffrey A.; et al, ACS Chemical Biology, 2009, 4(4), 261-267

Production Method 11

Reaction Conditions
1.1 Reagents: Triethylamine ,  Sulfur trioxide-pyridine complex Solvents: Dimethyl sulfoxide ,  Dichloromethane ;  rt → -10 °C; 60 min, -10 °C; 15 h, rt
2.1 Reagents: Monosodium phosphate ,  Sodium hypochlorite Solvents: Dimethyl sulfoxide ,  Water ;  2 h, rt; 2 h, rt
2.2 Reagents: Sodium bicarbonate Solvents: Water ;  15 h, rt
2.3 Reagents: Phosphoric acid ;  pH 2
Reference
Production of amorphadiene in yeast, and its conversion to dihydroartemisinic acid, precursor to the antimalarial agent artemisinin
Westfall, Patrick J.; et al, Proceedings of the National Academy of Sciences of the United States of America, 2012, 109(3),

Production Method 12

Reaction Conditions
Reference
Synergistic effect of coronatine and sorbitol on artemisinin production in cell suspension culture of Artemisia annua L. cv. Anamed
Salehi, Maryam; et al, Plant Cell, 2019, 137(3), 587-597

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