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CAS No. : | 1166-52-5 | MDL No. : | MFCD00002195 |
Formula : | C19H30O5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RPWFJAMTCNSJKK-UHFFFAOYSA-N |
M.W : | 338.44 | Pubchem ID : | 14425 |
Synonyms : |
Lauryl gallate;Gallic Acid dodecyl ester;Progallin LA;Nipagallin LA;NSC 133463;Gallic Acid lauryl ester
|
Num. heavy atoms : | 24 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.63 |
Num. rotatable bonds : | 13 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 96.67 |
TPSA : | 86.99 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.23 cm/s |
Log Po/w (iLOGP) : | 3.48 |
Log Po/w (XLOGP3) : | 5.83 |
Log Po/w (WLOGP) : | 4.88 |
Log Po/w (MLOGP) : | 3.12 |
Log Po/w (SILICOS-IT) : | 4.59 |
Consensus Log Po/w : | 4.38 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.94 |
Solubility : | 0.0039 mg/ml ; 0.0000115 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -7.43 |
Solubility : | 0.0000126 mg/ml ; 0.0000000373 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -5.17 |
Solubility : | 0.00229 mg/ml ; 0.00000676 mol/l |
Class : | Moderately soluble |
PAINS : | 1.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.89 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280 | UN#: | N/A |
Hazard Statements: | H317 | 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 |
---|---|---|
82% | With sulfuric acid; at 100.0℃; for 0.833333h;Microwave irradiation; | General procedure: A microwave vial was loaded with gallic acid 1 (0.3mmol, 50mg), the corresponding alcohol (0.9mmol), and concentrated H2SO4 (0.07mL). The reaction vessel was sealed and irradiated in a microwave reactor at 100C for 50min. After cooling, volatiles were evaporated to dryness and the residue was dissolved in ethyl acetate (30mL) and washed successively with saturated solutions of NaHCO3 (3×20mL) and NaCl (1×20mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under vacuum. The residue was then purified by column chromatography using hexane/EtOAc, (3:7) as the eluent. Melting points and characterization of compounds 2-7 were consistent with those found in the literature [25d]. In our case, the following yields were obtained: 2 (70%), 3 (97%), 4 (83%), 5 (98%), 6 (96%), 7 (82%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Specific examples of such electron accepting compounds are as follows: ... isopropyl p-hydroxybenzoate, benzyl p-hydroxybenzoate, benzyl protocatechuate, stearyl gallate, lauryl gallate, octyl gallate, 1,3-bis(4-hydroxyphenylthio)-2-hydroxypropane, N,N'-diphenylthiourea, ... | ||
Specific examples of the color developer for use in the present invention are as follows: ... benzyl protocatechuate, stearyl gallate, lauryl gallate, octyl gallate, ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With camphor-10-sulfonic acid; In chloroform; at 60.0℃; for 16.0h; | General procedure: All alkyl gallates were protected with isopropylydene acetal. The corresponding alkyl gallate and camphor sulfonic acid in catalytic amounts were dissolved in dry chloroform, 2,2-dimethoxypropane was then added and the reaction mixture was stirred for 16 h at 60 C. NEt3 was then added in order to neutralize. Solvents were removed in vacuo and the crude was purified by flash chromatography with hexane/ethyl acetate by using different polarities depending on the alkyl group. Reactions yields rated from 40 to 60%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
> 73% | In tetrahydrofuran; | General procedure: were synthesized by the exchange reactions between esters 5-7 andtriphenylantimony(V) chloride in THF according to an earlier described method.36 The yield of the reaction products was more than 73%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5.8% | In aq. phosphate buffer; at 80.0℃; for 2.0h;pH 7.0; | General procedure: PG (0.930 g, 0.44 M), OG (0.993 g, 0.44 M), and DG (1.190 g,0.44 M) were incubated with 5 mL GO (4.4 M, 1:10) in 5.0 mL phosphate buffer (0.2 M, pH 7.0) at 80 C for 2 h, respectively. The reaction mixture was loaded onto a reverse phase silica gel C18 (ODS-A-HG,50 mum, YMC Co., Ltd, Kyoto, Japan) column (400 mm×16 mm i.d.) and eluted with 20, 40 and 60% methanol successively, and with 40% methanol to obtain the mono-GO adduct of PG (MG-PG, 120 mg; yield:10.2%); eluted with 50, 60, 75 and 80% methanol successively, with 75% methanol to obtain the mono-GO adduct of OG (MG-OG, 100 mg; yield: 8.4%); eluted with 50, 70, 90 and 95% methanol successively, and with 90% methanol to obtain the mono-GO adduct of DG (MG-DG, 80 mg; yield: 5.8%) |