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Chemical Structure| 3397-65-7 Chemical Structure| 3397-65-7

Structure of N-Lauroyl-Glu-OH
CAS No.: 3397-65-7

Chemical Structure| 3397-65-7

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Product Details of [ 3397-65-7 ]

CAS No. :3397-65-7
Formula : C17H31NO5
M.W : 329.43
SMILES Code : O=C(O)CC[C@@H](C(O)=O)NC(CCCCCCCCCCC)=O
MDL No. :MFCD06410798
InChI Key :AVBJHQDHVYGQLS-AWEZNQCLSA-N
Pubchem ID :93133

Safety of [ 3397-65-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 3397-65-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 23
Num. arom. heavy atoms 0
Fraction Csp3 0.82
Num. rotatable bonds 16
Num. H-bond acceptors 5.0
Num. H-bond donors 3.0
Molar Refractivity 90.38
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

103.7 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.62
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

4.18
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

3.34
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

2.08
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

3.41
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.13

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.46
Solubility 0.114 mg/ml ; 0.000347 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-6.07
Solubility 0.000283 mg/ml ; 0.000000858 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-3.9
Solubility 0.042 mg/ml ; 0.000127 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

Yes
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

Yes
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

Yes
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.34 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

1.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.56

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<2.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

3.19

Application In Synthesis of [ 3397-65-7 ]

* 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.

  • Downstream synthetic route of [ 3397-65-7 ]

[ 3397-65-7 ] Synthesis Path-Downstream   1~19

  • 1
  • [ 112-16-3 ]
  • [ 56-86-0 ]
  • [ 3397-65-7 ]
YieldReaction ConditionsOperation in experiment
The result of analysis of the crystals in the same manner as in Example 1 indicated that the yield of the N-lauroyl-L-glutamic acid was 87percent.
Preferred examples of which include:...N-lauroyl aspartic acidN-palmitoyl aspartic acidN-octanoyl aspartic acidN-acetyl glutamic acidN-lauroyl glutamic acidN-palmitoyl glutamic acidN-octanoyl glutamic acidN-acetyl arginine...
Examples of which include: ... N-octanoyl aspartic acid N-acetyl glutamic acid N-lauroyl glutamic acid N-palmitoyl glutamic acid ...
Preferred examples of which include: ... N-octanoyl aspartic acid N-acetyl glutamic acid N-lauroyl glutamic acid N-palmitoyl glutamic acid ...

  • 4
  • [ 143-07-7 ]
  • [ 56-86-0 ]
  • [ 3397-65-7 ]
YieldReaction ConditionsOperation in experiment
96.28% 20.44 g of lauric acid (content of 98%) and 20.84 g of N,N'-dicyclohexylcarbodiimide (DCC) (content: 99%) were added to a ball mill and ground for 30 min. Add 14.86 g of glutamic acid (99%) and 8.42 g of sodium bicarbonate. After continuing to grind for 45 min, a white solid product was obtained which was the target collector product. After analysis and testing, The collector product 2-lauroamide glutaric acid content is 52.12%, The yield of 2-lauroyl glutaric acid based on lauric acid was 96.28%.
  • 5
  • [ 143-07-7 ]
  • [ 142-47-2 ]
  • [ 3397-65-7 ]
  • 6
  • [ 3397-65-7 ]
  • [ 143-07-7 ]
  • [ 56-86-0 ]
  • 7
  • [ 112-16-3 ]
  • Wang resin-bound Fmoc-L-glutamic acid [ No CAS ]
  • [ 3397-65-7 ]
  • 10
  • [ 110-89-4 ]
  • [ 3397-65-7 ]
  • N-lauroyl-L-glutamic acid di-piperidyl amide [ No CAS ]
  • 12
  • [ 143-07-7 ]
  • lauric acid-sulfuric acid [ No CAS ]
  • [ 56-86-0 ]
  • [ 7783-05-3 ]
  • [ 3397-65-7 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; triethylamine; In water; 1,2-dichloro-ethane; acetone; EXAMPLE 1 Lauric acid 20 g was dissolved in 80 ml 1.2-dichloroethane and then 10 g triethylamine was added. The resulting solution was held at -2 - 5C and 8 g sulfuric anhydride was added dropwise with stirring. The reaction mixture was stirred at that temperature for 50 minutes and a solution of lauric acid-sulfuric acid mixed acid anhydride was prepared and employed in the following acylation. Sodium hydroxide 8 g was added to a suspension of 14.7 g L-glutamic acid in 72 ml water and 48 ml acetone. The resulting solution of disodium L-glutamate was cooled to 0C and 10 ml of 10 N aqueous sodium hydroxide solution and the mixed acid anhydride prepared in the above was added drop by drop under stirring while the pH was controlled to 12 - 13. This reaction solution was stirred for 1 hour at 0C. Thereafter, the reaction mixture was concentrated under reduced pressure to distill off the solvent. The residue was adjusted to a pH 1 with 6 N sulfuric acid. The crude crystals of N-lauroyl-L-glutamic acid precipitated, and were filtered and dried (25.7 g). They were washed with petroleum benzine and 23.2 g of the purified acid were recovered by filtration (70.3% yield) M.P. 102 - 105C. After recrystallization from ethanol-petroleum benzine, the elemental analysis was as follows:
  • 13
  • [ 3397-65-7 ]
  • [ 557-34-6 ]
  • N-lauroyl-L-glutamic acid zinc salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; A zinc salt of lauroyl-L-glutamic acid was synthesized by the following method. Lauroyl-L-glutamic acid synthesized by a standard method (250 mg, 0.76 mmol) was dissolved in 10 ml of ethyl alcohol. An ethanol solution of 1percent zinc acetate (Wako Pure Chemical Industries, Ltd.) was prepared separately. This 1percent zinc acetate (18.4 ml) (0.84 mmol of zinc acetate, 1.1 equivalent weight of lauroyl-L-glutamic acid) was added to 10 ml of the previously prepared ethyl alcohol solution of lauroyl-L-glutamic acid, and the precipitate was separated by filtration. The precipitate was then washed with water, ethanol, and acetone, and then dried under reduced pressure. 200 mg of zinc salt of lauroyl-L-glutamic acid was obtained. The zinc salt of lauroyl glycine and the zinc salt of lauroyl-L-histidine were synthesized by reacting a lauroyl amino acid, synthesized in accordance with a standard method, with zinc acetate in the same manner as above, respectively. The results of elemental analysis of these compounds are shown in the Table 1. TABLE 1 Composition (percent) Ratio of lauroyl amino acid/ Compound Carbon Hydrogen Nitrogen Oxygen Zinc zinc Zinc salt of Calculated 51.9 7.4 3.6 20.4 16.7 1.0 lauroyl-L- value glutamic acid Measured 51.8 7.5 3.8 20.1 16.6 value Zinc salt of Calculated 58.2 9.0 4.8 16.6 11.3 1.9 lauroyl value glycine Measured 58.1 9.0 5.1 16.3 12.0 value Zinc salt of Calculated 58.6 8.1 11.4 13.0 8.9 1.7 lauroyl-L- value histidine Measured 55.0 8.1 11.2 Not 9.9 value measured
  • 14
  • [ 113493-05-3 ]
  • [ 3397-65-7 ]
  • 15
  • [ 112-18-5 ]
  • [ 3397-65-7 ]
  • C14H31N*C17H31NO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 20℃; for 48h; The CnGlu analogues were synthesized in our laboratory via a reaction of glutamic acid with octa-, deca-, dodeca-, tetradeca-,or hexadecanoyl chloride in the presence of triethylamine. C12DMA was purchased from Tokyo Chemical Industry and used without further purification. The acid-type CnGlu (1 equiv) was mixed with C12DMA (3 equiv) in ethanol at room temperature for 48 h under magnetic stirring. Then, the solvent was evaporated. The residue was recrystallized from either acetone or a mixture of hexane/ethyl acetate. After filtration, the residue was dried under reduced pressure. We confirmed the formation of a 1:1 stoichiometric complex of CnGlu-C12DMA on the basis of 1H NMR (JEOL-ECP 500 MHz) and ESI-MS (FT-ICR MS Varian 910-MS) data. These characterization data are shown in Supporting Information, Table S1. In typical experiments, the complex (3 wtpercent) was mixed with a NaOH aqueous solution, and the system was heated up to 80 °C. Then the solution was stirred and finally kept for 4 days at a constant temperature of 25 °C. The sample pH was controlled by changing the NaOH concentration.
  • 16
  • [ 3397-65-7 ]
  • N-lauroyl-L-glutamic acid sodium salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With sodium hydroxide; In ethanol; at 50 - 70℃; To a 1000 mL three-necked flask equipped with a thermometer and stirred, 329.5 g (1 mol) of lauroylglutamic acid was added, Anhydrous ethanol 659g, Heating up to 50 ~ 60 deg C to dissolved completely ,A phase transfer catalyst PEG-400 was added, 40 g of a granular sodium hydroxide solid was added, 50 ~ 70 deg C under the reaction of 20 ~ 30min, Cooling -5 ~ 5 deg C, Precipitation of white flaky crystals, Filter, After drying, To give 350 g of sodium lauroyl glutamate, Content of 98percent, Yield 99percent. The filtrate was dehydrated by 4A type molecular sieve, filtered and then subjected to atmospheric distillation, Distillation temperature 80 ~ 90 deg C, To obtain a fraction of anhydrous ethanol, The remaining liquid is polyethylene glycol, Are returned to the initial section for recycling. After the molecular sieve drying is activated by drying, Repeated use.
  • 17
  • Nα-lauroyl-arginine ethyl ester [ No CAS ]
  • [ 3397-65-7 ]
  • lauroyl arginine ethyl ester lauroylglutamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; water; at 60℃; Weigh lauroyl arginine ethyl ester 76.9 g (0.2 ml), Add 30 mL of ethanol, 60 ° C Water bath dissolved; (2) 0. lmol of lauroylglutamic acid by adding , stirring mixed hook, get salt system; will be obtained in the system vacuum distillation, remove the ethanol; ( 4) the resulting product lauroyl arginine ethyl ester lauroyl glutamate salt is yellow liquid, Freezing point 14 ° C.
  • 18
  • [ 111-82-0 ]
  • [ 142-47-2 ]
  • [ 3397-65-7 ]
YieldReaction ConditionsOperation in experiment
88.67% With magnesium oxide; potassium oxide; at 20 - 40℃; for 3h;pH 10 - 13; The molar ratio of raw material methyl laurate and sodium glutamate of 1.8: 0.7 was chosen to mix potassium oxide in a molar ratio of 2: 1And magnesium oxide is a metal oxide catalyst, and the catalyst is added in an amount of 0.05 wtpercent of the total amount of the reactants.The synthesis was prepared according to the one-step synthesis method in Example 1, in which the reaction temperature of the primary mixer was generally controlled at20 to 30 degrees, in particular, a mixer inlet temperature control at 25 degrees, a mixer outlet temperature control at25 degrees; pH maintained at 10. The reaction temperature of the secondary mixer is generally controlled between 30 and 40 degrees. Specifically, the secondary mixingThe feed inlet temperature control 35 degrees, two mixer outlet temperature control at 35 degrees; pH maintained at 13.After the reaction was completed, 0.069percent methanol was separated to obtain lauroyl glutamic acid having an active content of 88.67percentSodium, purity up to 98percent.
  • 19
  • [ 111-82-0 ]
  • C16H36P(1+)*C5H7NO4(2-)*H(1+) [ No CAS ]
  • [ 3397-65-7 ]
YieldReaction ConditionsOperation in experiment
15% at 80℃; for 54h;Inert atmosphere; General procedure: Commercially available ionized liquid tetrabutylphosphonium glycinate (Gly-TBP, manufactured by Katayama Pharmaceutical Co., Ltd., colorless transparent liquid, moisture content: 0.11 mass percent) was used as the component (A).In a high purity argon atmosphere, Lau-OMe was added to 1 kg of the above Gly-TBP so that the amount of methyl laurate (Lau-OMe, Wako Pure Chemical Industries, Ltd.) was 500 mmol (Gly-TBP: Lau-OMe molar ratio = 6: 1). After thorough stirring of the obtained solution, it was confirmed that the whole solution became homogeneous, and then the reaction was started by heating to 60 ° C. while stirring in a water bath. Each time-lapse sample was analyzed by HPLC to confirm formation of N-acylamino acid (N-lauroylglycine). After 86 hours, the yield of N-acylamino acid (N-lauroylglycine) was about 82percent
 

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