Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 85031-59-0 | MDL No. : | MFCD16876168 |
Formula : | C15H24O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JYGAZEJXUVDYHI-DGTMBMJNSA-N |
M.W : | 236.35 | Pubchem ID : | 11020893 |
Synonyms : |
Dihydroqinghao acid
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.8 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 71.29 |
TPSA : | 37.3 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.0 cm/s |
Log Po/w (iLOGP) : | 2.68 |
Log Po/w (XLOGP3) : | 3.86 |
Log Po/w (WLOGP) : | 3.73 |
Log Po/w (MLOGP) : | 3.44 |
Log Po/w (SILICOS-IT) : | 2.65 |
Consensus Log Po/w : | 3.27 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -3.61 |
Solubility : | 0.0587 mg/ml ; 0.000248 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.34 |
Solubility : | 0.0108 mg/ml ; 0.0000457 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -2.08 |
Solubility : | 1.98 mg/ml ; 0.00839 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 4.17 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With palladium on activated charcoal; hydrogen In chloroform at 20℃; | Dissolve 100 g (0.43 mol) of artemisinic acid in 800 mL of chloroform.At room temperature, hydrogen pressure 1 bar, 1.5g palladium carbon as a catalyst, reaction overnight, diatomaceous earth filtration,Wash with chloroform and recover the solvent under reduced pressure.The solid product dihydroartemisinic acid 99 g (0.42 mol) was obtained in 98percent yield. |
95% | Stage #1: With hydroxylamine; sodium hydroxide; hydroxylamine-O-sulfonic acid In methanol; water at -5 - 0℃; Stage #2: With hydrogenchloride In methanol; water |
Example 3: Synthesis of dihydroartemisinic acid la by diimine generation from hydroxylamine and HOSA/NaOH in methanol at -5°C to 0°C2.34 g (0.01 mol) of artemisinic acid Ilia was dissolved in 20 mL of MeOH. Then 1 .98 g (0.03 mol) of hydroxylamine (50 percent in water) and 5.65 g (0.045 mol) of HOSA (dissolved in 10 mL of water) were added continuously while a pH 9 was held maintained with a 32percent aqueous NaOH solution. The temperature was adjusted to between -5°C and 0°C. After complete addition the reaction mixture was stirred for one additional hour until no pH change was detectable. The complete consumption of artemisinic acid was confirmed with RP-HPLC analysis. Then the reaction mixture was acidified with dilute aqueous hydrochloride acid to pH 2. The product was extracted with MTBE, dried over magnesium sulfate and the solvent was evaporated to give 2.25 g (95percent) of the title compound which crystallized on standing. The diastereomeric ratio in the unpurified product as determined by 1 H- NMR and LC/MS analysis was 98:2 in favour of the desired stereoisomer la. |
94% | With hydrazine hydrate In isopropyl alcohol at 15 - 40℃; for 10 h; | 15 g (64 mmol) of artemisinic acid were initially charged in 45 ml of isopropanol. At 15-25 °C, 9.81 g (192 mmol) of hydrazine hydrate were added dropwise to the artemisinic acid solution. The reaction solution were then transferred into a heatable chromatography column with bottom glass frit and, at 40 °C, gassed with 5percent strength synthetic air (5percent O2 + 95percent N2) via the bottom glass frit for 10 hours. After complete conversion into dihydroartemisinic acid (checked by Raman spectroscopy) the reaction solution was discharged into a vessel and the chromatography column was washed twice with 15 ml of isopropanol. The reaction solution (pH 8) was adjusted to pH 3-4 using at least 40 ml of 2N hydrochloric acid. After addition of 75 ml of methylene chloride, the two-phase mixture was stirred vigorously for 10 minutes. Organic and aqueous phase were then separated. The organic phase was extracted once more with 50 ml of water. The resulting methylene chloride solution comprises 14.2 g of dihydroartemisinic acid in a yield of 94percent and a diastereomer ratio of 97:3 (HPLC). |
94% | With hydrazine hydrate In isopropyl alcohol at 15 - 40℃; for 10 h; | 15 g (64 mmol) of artemisinic acid were initially charged in 45 ml of isopropanol. At 15- 25°C, 9.81 g (192 mmol) of hydrazine hydrate were added dropwise to the artemisinic acid solution. The reaction solution were then transferred into a heatable chromatography column with bottom glass frit and, at 40 °C, gassed with 5percent strength synthetic air (5percent 02 + 95percent N2) via the bottom glass frit for 10 hours. After complete conversion into dihydroartemisinic acid (checked by Raman spectroscopy) the reaction solution was discharged into a vessel and the chromatography column was washed twice with 15 ml of isopropanol. The reaction solution (pH 8) was adjusted to pH 3-4 using at least 40 ml of 2N hydrochloric acid. After addition of 75 ml of methylene chloride, the two-phase mixture was stirred vigorously for 10 minutes. Organic and aqueous phase were then separated. The organic phase was extracted once more with 50 ml of water. The resulting methylene chloride solution comprises 14.2 g of dihydroartemisinic acid in a yield of 94percent and a diastereomer ratio of 97:3 (HPLC). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77.7% | With sodium dihydrogenphosphate In water; dimethyl sulfoxide at 20℃; | Dihydroartemisinic acid was prepared according to the procedure described inBaI, B. S.; Childers, W.E.; Pinnick, H. W., Tetrahedron, 1981, 37, 2091-2096; and Dalcanale, E.; Montanari, F. J., J. Org. Chem., 1986, 51, 569-569, both of which are incorporated herein by reference. To a 100 mL Ace Glass two-piece reactor equipped with a mechanical stirrer, were added 0.281 g (1.28 mmol) of dihydroartemisinic aldehyde and 24 mL of dimethyl sulfoxide (DMSO). The mixture was stirred and a solution of 0.172 g (1.90 mmol) OfNaOCl2 and 0.966 g (8.30 mmol) OfNaH2PO4 in 12 mL of water was added at ambient temperature via syringe pump over four hours. After an additional hour GC-MS analysis showed the reaction to be complete. The reaction was diluted with 40 mL of water and acidified to pH 2 with concentrated phosphoric acid (H3PO4). Vacuum filtration of the resulting suspension afforded 0.234 g (77.7percent) of dihydroartemisinic acid as very fine white needles which exhibited a GC-MS chromatogram and 1H NMR spectrum similar to those of an authentic sample. |
[ 2305-26-2 ]
(1R,2S)-rel-Cyclohex-4-ene-1,2-dicarboxylic acid
Similarity: 0.84
[ 5708-19-0 ]
(S)-Cyclohex-3-enecarboxylic acid
Similarity: 0.84
[ 5709-98-8 ]
(R)-Cyclohex-3-enecarboxylic acid
Similarity: 0.84
[ 2305-26-2 ]
(1R,2S)-rel-Cyclohex-4-ene-1,2-dicarboxylic acid
Similarity: 0.84
[ 5708-19-0 ]
(S)-Cyclohex-3-enecarboxylic acid
Similarity: 0.84
[ 5709-98-8 ]
(R)-Cyclohex-3-enecarboxylic acid
Similarity: 0.84
[ 2305-26-2 ]
(1R,2S)-rel-Cyclohex-4-ene-1,2-dicarboxylic acid
Similarity: 0.84
[ 5708-19-0 ]
(S)-Cyclohex-3-enecarboxylic acid
Similarity: 0.84
[ 5709-98-8 ]
(R)-Cyclohex-3-enecarboxylic acid
Similarity: 0.84