1.1
Catalysts:
Cytochrome P450
Solvents:
Water
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- 80286-58-4
Artemisic acid | 80286-58-4
(1S,5R,9R,12R,13R)-1,5,9-Trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-ol
CAS No.: 71939-50-9
(1R,5R,9S,12R)-8,12-Dimethyl-4-methylidene-2,13-dioxatetracyclo[7.5.0.01,5.012,14]tetradecan-3-one
CAS No.: 50906-56-4
Artemisinic acid is a white crystalline powder, which can be dissolved in methanol \ ethanol \dmso and other organic solvents, and is derived from the composite plant Artemisia annua
- 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
- QING HAO 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
- QING HAU ACID
- LMPR0103190015
- ARTEMISININIC ACID
- 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
- MDL：N/A
- InChIKey：PLQMEXSCSAIXGB-SAXRGWBVSA-N
- 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
- SMILES：C([C@@H]1CC[C@@H](C)[C@@H]2CCC(=C[C@H]12)C)(=C)C(=O)O
Computed Properties
-
Exact Mass: 234.33g/mol
-
Surface Charge: 0
-
XLogP3: 3.8
-
Hydrogen Bond Donor Count: 1
-
Hydrogen Bond Acceptor Count: 2
-
Rotatable Bond Count: 2
-
Monoisotopic Mass: 234.16198g/mol
-
Monoisotopic Mass: 234.16198g/mol
-
Topological Polar Surface Area: 37.3Ų
-
Heavy Atom Count: 17
-
Complexity: 367
-
Isotope Atom Count: 0
-
Defined Atom Stereocenter Count: 4
-
Undefined Atom Stereocenter Count : 0
-
Defined Bond Stereocenter Count: 0
-
Undefined Bond Stereocenter Count: 0
-
Covalently-Bonded Unit Count: 1
Experimental Properties
- LogP: 3.64580
- PSA: 37.30000
- Refractive Index: 1.504
- Boiling Point: 373.6℃/760mmHg
- Melting Point: 129-131 ºC
- Flash Point: 273.3°C
- Color/Form: Colorless crystal
- Solubility: Soluble in methanol, ethanol, DMSO and other organic solvents, soluble in chloroform, slightly soluble in sodium bicarbonate aqueous solution
- Density: 1.019
- Safety Instruction：H303 may be harmful by ingestion +h313 may be harmful by skin contact +h333 may be harmful by inhalation
- Hazard Statement：H302-H315-H319-H335
- Warning Statement：P261-P305+P351+P338
- Storage Condition：Sealed in dry,2-8°C
- Signal Word：Warning
Synthetic Circuit 1
Reaction Conditions
+ Expand
Reference
A chicory cytochrome P450 mono-oxygenase CYP71AV8 for the oxidation of (+)-valencene
,
FEBS Letters,
2011,
585(1),
178-182
Synthetic Circuit 2
Reaction Conditions
+ Expand
1.1
-
2.1 Reagents: Potassium hydroxide , Borate(1-), tetrahydro-t4-, sodium
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
,
Huaxue Xuebao,
1991,
49(12),
1514-17
Synthetic Circuit 3
Reaction Conditions
+ Expand
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
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
,
Nature Catalysis,
2021,
4(10),
892-900
Synthetic Circuit 4
Reaction Conditions
+ Expand
1.1
Reagents:
Potassium hydroxide
Reference
Biosynthesis of arteannuin. II. Chemical synthesis of the precursors [15-2H]- and [15-3H]-arteannuic acid
,
Huaxue Xuebao,
1991,
49(12),
1514-17
Synthetic Circuit 5
Reaction Conditions
+ Expand
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
,
Chemistry - A European Journal,
2015,
21(11),
4368-4376
Synthetic Circuit 6
Reaction Conditions
+ Expand
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
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
,
Nature Catalysis,
2021,
4(10),
892-900
Synthetic Circuit 7
Reaction Conditions
+ Expand
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
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
,
Organic Letters,
2023,
25(1),
277-281
Synthetic Circuit 8
Reaction Conditions
+ Expand
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
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
,
Nature Catalysis,
2021,
4(10),
892-900
Synthetic Circuit 9
Reaction Conditions
+ Expand
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
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
,
Organic Letters,
2023,
25(1),
277-281
Synthetic Circuit 10
Reaction Conditions
+ Expand
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
,
Nature Catalysis,
2021,
4(10),
892-900
Synthetic Circuit 11
Reaction Conditions
+ Expand
1.1
Solvents:
Water
;
120 h, 30 °C
Reference
Production of the antimalarial drug precursor artemisinic acid in engineered yeast
,
Nature (London,
2006,
440(7086),
940-943
Synthetic Circuit 12
Reaction Conditions
+ Expand
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
,
Huaxue Xuebao,
1991,
49(12),
1514-17
- 1. Artemisinic acid: A promising molecule potentially suitable for the semi-synthesis of artemisinin Jianqiang Kong,Yan Yang,Wei Wang,Kedi Cheng,Ping Zhu RSC Adv. 2013 3 7622
- 2. Synthesis of artemisinic acid derived glycoconjugates and their anticancer studies Tharun K. Kotammagari,Sayantan Paul,Ganesh K. Barik,Manas K. Santra,Asish K. Bhattacharya Org. Biomol. Chem. 2020 18 2252
- 3. Synthetic chemistry fuels interdisciplinary approaches to the production of artemisinin Michael A. Corsello,Neil K. Garg Nat. Prod. Rep. 2015 32 359
- 4. Synthetic biology Ali Tavassoli Org. Biomol. Chem. 2010 8 24
- 5. Yeast-based genome mining, production and mechanistic studies of the biosynthesis of fungal polyketide and peptide natural products Yuta Tsunematsu,Kan'ichiro Ishiuchi,Kinya Hotta,Kenji Watanabe Nat. Prod. Rep. 2013 30 1139
- 6. Industrial biotechnology—the future of green chemistry? Stefanie Wenda,Sabine Illner,Annett Mell,Udo Kragl Green Chem. 2011 13 3007
- 7. Whole-cell biocatalysis for selective and productive C–O functional group introduction and modification Manfred Schrewe,Mattijs K. Julsing,Bruno Bühler,Andreas Schmid Chem. Soc. Rev. 2013 42 6346
- 8. Synthesis of chemicals by metabolic engineering of microbes Xinxiao Sun,Xiaolin Shen,Rachit Jain,Yuheng Lin,Jian Wang,Jing Sun,Jia Wang,Yajun Yan,Qipeng Yuan Chem. Soc. Rev. 2015 44 3760
- 9. Tools and strategies of systems metabolic engineering for the development of microbial cell factories for chemical production Yoo-Sung Ko,Je Woong Kim,Jong An Lee,Taehee Han,Gi Bae Kim,Jeong Eum Park,Sang Yup Lee Chem. Soc. Rev. 2020 49 4615
- 10. Comparative in vitro cytotoxicity and binding investigation of artemisinin and its biogenetic precursors with ctDNA Neha Maurya,Khalid Imtiyaz,M. Moshahid Alam Rizvi,Khaled Mohamed Khedher,Prashant Singh,Rajan Patel RSC Adv. 2020 10 24203
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1 mL * 10 mM (in DMSO) 1000mg 100mg 10mg 10mM*1 mL in DMSO 10mM*1mLinDMSO 1mg 20mg 250MG 25mg 500MG 50mg 5mg+ multiple choice
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1PlusChem A2B Chem LLC Aaron abcr ChemFaces ChemScence Chengdu Biopurify Phytochemicals Ltd DC Chemicals eNovation Chemicals LLC MedChemExpress Nature Science Technologies Selleck中国 TargetMol Chemicals TRC 合肥博美生物科技有限责任公司 上海吉至生化科技有限公司 上海陶术生物科技有限公司 上海贤鼎生物科技有限公司 武汉安捷凯生物医药科技有限公司+ multiple choice
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| Brand:Acmec | Supplier:上海吉至生化科技有限公司 | ||||||
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| No. | Purity | Stock | Specification | Price | update time | operate | |
| A98560-20mg | 现货 | 20mg | ¥1598.0 | 10 Sep. 2021 | |||
| Brand:bomeibio | Supplier:合肥博美生物科技有限责任公司 | ||||||
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| Brand:selleck | Supplier:Selleck中国 | ||||||
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