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Artemisinic acid

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Name

Artemisinic acid

EINECS N/A
CAS No. 80286-58-4 Density 1.019 g/cm3
PSA 37.30000 LogP 3.64580
Solubility N/A 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 N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 80286-58-4 (artemisic acid) Hazard Symbols N/A
Synonyms

Arteannuic acid;Artemisininic acid;Qing Hao acid;

Article Data 5

Artemisinic acid Synthetic route

125184-95-4

dehydroartemisinyl alcohol

80286-58-4

artemisinic acid

Conditions
ConditionsYield
With Jones reagent In acetone at 20℃;100%
64-17-5

ethanol

50-99-7

D-glucose

80286-58-4

artemisinic acid

Conditions
ConditionsYield
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
ConditionsYield
With Tetradecanoic acid 1-methylethyl ester Reagent/catalyst; Enzymatic reaction;
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
ConditionsYield
With Tetradecanoic acid 1-methylethyl ester Reagent/catalyst; Enzymatic reaction;
80286-58-4

artemisinic acid

82869-24-7

methyl artemisinate

Conditions
ConditionsYield
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

Conditions
ConditionsYield
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%
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
ConditionsYield
In diethyl ether at 0℃; for 10h;98%
80286-58-4

artemisinic acid

110715-68-9

(S)-dihydroartemisinic acid

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%

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

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