Artemisinic acid supplier | CasNO.80286-58-4

Name
artemisic acid
EINECS
CAS No. 80286-58-4
Article Data5
CAS DataBase
Density 1.019 g/cm³
Solubility
Melting Point 129-131 °C
Formula C₁₅H₂₂O₂
Boiling Point 373.563 °C at 760 mmHg
Molecular Weight 234.338
Flash Point 273.336 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Arteannuic acid;Artemisininic acid;Qing Hao acid;
PSA 37.30000
LogP 3.64580

Synthetic route

: 125184-95-4
dehydroartemisinyl alcohol

: 80286-58-4
artemisinic acid

Conditions

Conditions	Yield
With Jones reagent In acetone at 20℃;	100%

: 64-17-5
ethanol

: 50-99-7
D-glucose

: 80286-58-4
artemisinic acid

Conditions

Conditions	Yield
With Tetradecanoic acid 1-methylethyl ester; artemisinic acid producing yeast strain In water for 123.4h; Product distribution / selectivity; Enzymatic reaction;

: 64-17-5
ethanol

A: artemisinic aldehyde

B: 80286-58-4
artemisinic acid

C: 92692-39-2
(1R,4R,4aS,8aR)-4,7-dimethyl-1-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene

D: 125184-95-4
dehydroartemisinyl alcohol

Conditions

Conditions	Yield
With Tetradecanoic acid 1-methylethyl ester Reagent/catalyst; Enzymatic reaction;

...Expand

: 64-17-5
ethanol

A: 80286-58-4
artemisinic acid

B: 92692-39-2
(1R,4R,4aS,8aR)-4,7-dimethyl-1-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene

C: 125184-95-4
dehydroartemisinyl alcohol

Conditions

Conditions	Yield
With Tetradecanoic acid 1-methylethyl ester Reagent/catalyst; Enzymatic reaction;

...Expand

: 186581-53-3, 908094-01-9
diazomethane

: 80286-58-4
artemisinic acid

: 82869-24-7
methyl artemisinate

Conditions

Conditions	Yield
In diethyl ether at 0℃;	100%
In diethyl ether at 0℃;	99%
In diethyl ether for 0.333333h; Ambient temperature;	98%

: 80286-58-4
artemisinic acid

: 85031-59-0, 110715-68-9, 126643-10-5
dihydroartemisinic acid

Conditions

Conditions	Yield
With lithium borohydride; nickel dichloride In methanol for 2h; Ambient temperature;	100%
With C48H50Cl4N2O2P2Ru3; hydrogen; sodium hydrogencarbonate In methanol at 0℃; under 22502.3 Torr; for 36h; Autoclave;	98%
With palladium on activated charcoal; hydrogen In chloroform at 20℃; under 750.075 Torr; Solvent; Pressure; Reagent/catalyst;	98%

: 186581-53-3, 908094-01-9
diazomethane

: 80286-58-4
artemisinic acid

: 150665-64-8
(S)-3-((1R,4R,4aS,8aR)-4,7-Dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-1-yl)-4,5-dihydro-3H-pyrazole-3-carboxylic acid methyl ester

Conditions

Conditions	Yield
In diethyl ether at 0℃; for 10h;	98%

: 80286-58-4
artemisinic acid

: 110715-68-9
(S)-dihydroartemisinic acid

Conditions

Conditions	Yield
With C48H50Cl4N2O2P2Ru3; hydrogen; sodium hydrogencarbonate In methanol at 0℃; under 22502.3 Torr; for 36h; Autoclave;	98%
With dihydrogen peroxide; hydrazine hydrate In ethanol at 0 - 20℃;	86%

: 80286-58-4
artemisinic acid

: 161022-41-9
dihydroartemisinic acid

Conditions

Conditions	Yield
With hydrogen; potassium hydroxide In water; toluene at 0 - 60℃; under 76005.1 Torr; for 12h; Reagent/catalyst; Solvent; Autoclave; enantioselective reaction;	97.4%
With hydrogen; Wilkinson's catalyst In methanol under 1551.49 - 1913.5 Torr; for 289h; Product distribution / selectivity; Parr apparatus;
With tris(triphenylphosphine)ruthenium(II) chloride; C48H50N2O2P2Ru; hydrogen; triethylamine In methanol at 0℃; under 15001.5 Torr; for 24h; Autoclave; enantioselective reaction;	n/a

: 80286-58-4
artemisinic acid

: 2450-71-7
Propargylamine

: 2-((1R,4R,4aS,8aR)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)-N-(prop-2-yn-1-yl)acrylamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 25℃; for 6h; Inert atmosphere;	95%
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 25℃; for 6h; Inert atmosphere;	95%

: 80286-58-4
artemisinic acid

: 80-48-8
methyl p-toluene sulfonate

: 82869-24-7
methyl artemisinate

Conditions

Conditions	Yield
With potassium carbonate In acetone for 1h; Heating;	94%

: 80286-58-4
artemisinic acid

: 107-19-7
propargyl alcohol

: prop-2-yn-1-yl 2-((1R,4R,4aS,8aR)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)acrylate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 25℃; for 12h;	94%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 25℃; for 12h;	94%

: 17376-04-4
2-phenethyl iodide

: 80286-58-4
artemisinic acid

: 2-((1R,4R,4aS,8aS)-4,7-Dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-1-yl)-5-phenyl-pentanoic acid

Conditions

Conditions	Yield
With triethyl borane; tri-n-butyl-tin hydride In hexane at 20℃; for 16h; Addition;	72%

: 80286-58-4
artemisinic acid

: 125184-95-4
dehydroartemisinyl alcohol

Conditions

Conditions	Yield
Stage #1: artemisinic acid With lithium aluminium tetrahydride In tetrahydrofuran at 70℃; for 15h; Heating / reflux; Stage #2: With sodium hydroxide; water In tetrahydrofuran for 0.166667h;	65%
With diisobutylaluminium hydride
Multi-step reaction with 2 steps 1: 99 percent / diethyl ether / 0 °C 2: 82 percent / DIBAL / CH2Cl2 / -78 °C View Scheme

: 80286-58-4
artemisinic acid

A: 118059-19-1
3-β-hydroxyartemisinic acid

B: 3β,15-dihydroxyartemisinic acid

Conditions

Conditions	Yield
With endophytic fungus Trichothecium roseum CIMAPN1 In aq. phosphate buffer; acetone at 28℃; for 336h; pH=6; Microbiological reaction; stereoselective reaction;	A 51.1% B 37.3%

: 80286-58-4
artemisinic acid

A: 3β-hydroxyartemisinic acid

B: 3β,15-dihydroxyartemisinic acid

C: 9-oxo-arteannuinic acid

Conditions

Conditions	Yield
With cell culture of endophytic fungus Trichothecium roseum In acetone for 336h; Microbiological reaction;	A 50.4% B 32.2% C 5.2%

...Expand

: 50-99-7
D-glucose

: 80286-58-4
artemisinic acid

: artemisinic acid glucose ester

Conditions

Conditions	Yield
With whole-cell of E. coli BL21 culture at 25℃; for 72h; pH=7.0; aq. buffer; Enzymatic reaction;	18.6%

: 186581-53-3, 908094-01-9
diazomethane

: 80286-58-4
artemisinic acid

: 129165-35-1
methyl <2'R,4a'S,5'R,8'R>-2-(2',5'-dimethyl-2'-hydroperoxy-2',3',4',4a',5',6',7',8'-octahydronaphthalen-8'-yl)propenoate

Conditions

Conditions	Yield
With oxygen; rose bengal 1.) acetonitrile, -30 deg C, irradiation, 2.) ether, 0 deg C; Yield given. Multistep reaction;

: 186581-53-3, 908094-01-9
diazomethane

: 80286-58-4
artemisinic acid

A: 87391-99-9
2-(4,7-dimethyl-(1α-H),2,3,(4β-H),(4aα-H),5,6,(8aα-H)-octahydronaphthalen-1-yl)propionic acid methyl ester

B: 85788-54-1, 87391-99-9, 98575-64-5
11S-methyl arteannuinate

Conditions

Conditions	Yield
With sodium tetrahydroborate; nickel dichloride 1.) MeOH, -15 deg C, 2.) 30 min; Multistep reaction;

...Expand

: 80286-58-4
artemisinic acid

: 101020-89-7
dehydroqinghaosu

Conditions

Conditions	Yield
With oxygen; copper(II) bis(trifluoromethanesulfonate); rose bengal 1.) acetonitrile, -30 deg C, 2.) from -20 deg C to RT, 12 h; Yield given. Multistep reaction;

: 80286-58-4
artemisinic acid

A: 63968-64-9
C12H13O2(CH3)3(O)(OO)

B: 50906-56-4
(1R,5S,8R,9S,12R,14R)-8,12-dimethyl-4-methylidene-2,13-dioxatetracyclo[7.5.0.01,5.012,14]tetradecan-3-one

Conditions

Conditions	Yield
In water at 30℃; for 2h; cell-free extract from Artemisia annua L. (Asteraceae), EDTA, HEPES with DDT buffer, pH 7.15; Title compound not separated from byproducts;

: 80286-58-4
artemisinic acid

: arteannuin B

Conditions

Conditions	Yield
With oxygen; methylene blue In ethanol at 22℃; for 4h; Irradiation; Yield given;

: 80286-58-4
artemisinic acid

: 2-((1S,4R,4aS,6S,8aR)-6-Hydroxy-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-1-yl)-acrylic acid

Conditions

Conditions	Yield
microbial fermentation by Mucor mucedo; Yield given;

: 80286-58-4
artemisinic acid

A: 2-((1S,4R,4aS,6S,8aR)-6-Hydroxy-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-1-yl)-acrylic acid

B: 3-α-hydroxyartemisinic acid

Conditions

Conditions	Yield
microbial fermentation by Aspergilus flavipes; var. organism; Yield given. Yields of byproduct given;

: 80286-58-4
artemisinic acid

: 128261-36-9
2-((1R,4R,4aS,7R)-7-Hydroxy-4,7-dimethyl-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-yl)-acrylic acid

Conditions

Conditions	Yield
With dihydrogen peroxide; oxygen; triethyl phosphite; methylene blue 1.) irradiation, CH2Cl2, -78 deg C, 2.5 h; 2.) Et2O-petrol, rt, 30 min; 3.) t-BuOH; Yield given. Multistep reaction;

: 80286-58-4
artemisinic acid

A: 128261-36-9
2-((1R,4R,4aS,7R)-7-Hydroxy-4,7-dimethyl-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-yl)-acrylic acid

B: epi-deoxyarteannuin B

Conditions

Conditions	Yield
With oxygen; sodium carbonate; triphenylphosphine; methylene blue 1.) irradiation, CH2Cl2, -78 deg C, 2.5 h; 2.) to -15 deg C, 30 min; 3.) water, 100 deg C, 2h; Yield given. Multistep reaction. Yields of byproduct given;

: 80286-58-4
artemisinic acid

: epi-deoxyarteannuin B

Conditions

Conditions	Yield
With oxygen; methylene blue In dichloromethane at -78℃; for 2.5h; Irradiation;

: 75-77-4
chloro-trimethyl-silane

: 80286-58-4
artemisinic acid

: 195060-78-7
C18H30O2Si

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran at 0℃; for 0.25h;
With n-butyllithium 1) THF, 0 deg C, 15 min, 2) THF, 0 deg C, 15 min; Multistep reaction;

: 13154-24-0
triisopropylsilyl chloride

: 80286-58-4
artemisinic acid

: 195060-80-1
C24H42O2Si

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran at 0℃; for 0.25h;
With n-butyllithium 1) THF, 0 deg C, 15 min, 2) THF, 0 deg C, 15 min; Multistep reaction;

: 80286-58-4
artemisinic acid

: 18162-48-6
tert-butyldimethylsilyl chloride

: 195060-79-8
C21H36O2Si

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran at 0℃; for 0.25h;
With n-butyllithium 1) THF, 0 deg C, 15 min, 2) THF, 0 deg C, 15 min; Multistep reaction;

: 13154-24-0
triisopropylsilyl chloride

: 80286-58-4
artemisinic acid

: 195060-79-8
C21H36O2Si

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran at 0℃; for 0.25h;

: 80286-58-4
artemisinic acid

: 18162-48-6
tert-butyldimethylsilyl chloride

: 195060-80-1
C24H42O2Si

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran at 0℃; for 0.25h;

Artemisinic acid Specification

The Artemisinic acid, with the CAS registry number 80286-58-4, is also known as Arteannuic acid. It belongs to the product category of Miscellaneous Natural Products. This chemical's molecular formula is C₁₅H₂₂O₂ and molecular weight is 234.34. What's more, both its IUPAC name and systematic name are the same which is called 2-[(1R,4R,4aS,8aR)-4,7-Dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]prop-2-enoic acid.

Physical properties about Artemisinic acid are: (1)ACD/LogP: 5.11; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 3.91; (4)ACD/LogD (pH 7.4): 2.12; (5)ACD/BCF (pH 5.5): 281.08; (6)ACD/BCF (pH 7.4): 4.56; (7)ACD/KOC (pH 5.5): 895.70; (8)ACD/KOC (pH 7.4): 14.53; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 37.3 Å²; (13)Index of Refraction: 1.505; (14)Molar Refractivity: 68.127 cm³; (15)Molar Volume: 229.854 cm³; (16)Polarizability: 27.008×10^-24cm³; (17)Surface Tension: 34.031 dyne/cm; (18)Density: 1.019 g/cm³; (19)Flash Point: 273.336 °C; (20)Enthalpy of Vaporization: 68.177 kJ/mol; (21)Boiling Point: 373.563 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

Uses of Artemisinic acid: it is used to produce other chemicals. For example, it can react with qinghao acid to get methyl artemisinate. This reaction needs solvent diethyl ether at temperature of 0 °C. The reaction time is 30 min. The yield is 98 %.

Artemisinic acid can react with qinghao acid to get methyl artemisinate.

You can still convert the following datas into molecular structure:
(1) SMILES: OC(=O)C(=C)[C@@H]1CC[C@@H](C)[C@@H]2CCC(\C)=C/[C@H]12
(2) InChI: 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
(3) InChIKey: PLQMEXSCSAIXGB-SAXRGWBVSA-N

Product Name

artemisic acid

Synthetic route

Artemisinic acid Specification

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