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Chemical Structure| 623-65-4 Chemical Structure| 623-65-4

Structure of Palmitic anhydride
CAS No.: 623-65-4

Chemical Structure| 623-65-4

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Synonyms: Palmitic acid anhydride

4.5 *For Research Use Only !

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Product Details of [ 623-65-4 ]

CAS No. :623-65-4
Formula : C32H62O3
M.W : 494.83
SMILES Code : CCCCCCCCCCCCCCCC(OC(CCCCCCCCCCCCCCC)=O)=O
Synonyms :
Palmitic acid anhydride
MDL No. :MFCD00008992
InChI Key :QWZBEFCPZJWDKC-UHFFFAOYSA-N
Pubchem ID :69339

Safety of [ 623-65-4 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:3261
Packing Group:

Computational Chemistry of [ 623-65-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 35
Num. arom. heavy atoms 0
Fraction Csp3 0.94
Num. rotatable bonds 30
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 157.42
TPSA ?

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

43.37 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

7.88
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

14.55
Log Po/w (WLOGP)?

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

11.02
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.

7.0
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

12.03
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

10.5

Water Solubility

Log S (ESOL):?

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

-10.09
Solubility 0.0000000398 mg/ml ; 0.0000000001 mol/l
Class?

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

Insoluble
Log S (Ali)?

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

-15.56
Solubility 0.0 mg/ml ; 2.75e-16 mol/l
Class?

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

Insoluble
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

-11.45
Solubility 0.0000000017 mg/ml ; 0.0 mol/l
Class?

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

Insoluble

Pharmacokinetics

GI absorption?

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

Low
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

No
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

No
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.

1.01 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

1.0
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

1.0
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

2.0
Bioavailability Score?

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

0.55

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

2.0 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<3.0
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)

4.6

Application In Synthesis of [ 623-65-4 ]

* 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 [ 623-65-4 ]

[ 623-65-4 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 623-65-4 ]
  • [ 770-05-8 ]
  • hexadecanoic acid 2-hexadecanoylamino-1-(4-hexadecanoyloxy-phenyl)-ethyl ester [ No CAS ]
  • 2
  • [ 623-65-4 ]
  • [ 68-26-8 ]
  • [ 79-81-2 ]
YieldReaction ConditionsOperation in experiment
97.62% With aluminum oxide; In Petroleum ether; at 40℃; for 2.0h; (59.5 g, 0.12 mol) of palmitic anhydride was charged to a solution of (28.6 g, 0.1 mol) of vitamin A alcohol and 240 g of petroleum ether, heated slowly to 40C in a water bath, and 4.29 g of activated 200 mesh of basic alumina was added. Insulation reaction 2 hours, liquid tracking detection of vitamin A residual alcohol ? 0.3% to stop the antiShould, filter out the basic alumina, -12 cold treatment, filter residue, the filtrate for dissolution, obtainedLight yellow oily liquid product (51.2 g, 97.62% molar yield). The HPLC analysis of the product was in accordance with the standard. The product was analyzed by USP28. The biological titer was 1.781 million IU / g and the content was 98.3%.
  • 3
  • [ 623-65-4 ]
  • [ 57-10-3 ]
  • [ 50-81-7 ]
  • [ 137-66-6 ]
YieldReaction ConditionsOperation in experiment
91.3% (1)500g of concentrated sulfuric acid was added to the three-necked flask, add 50g of palmitic acid, stirring to dissolve Solution in concentrated sulfuric acid was added 50gL- ascorbic acid, 18 C reaction 15h; (2)50g palmitic anhydride was added to the reaction mixture, the temperature was raised to 28 C, the reaction 20h, then After adding 10g of activated carbon and stirred for 15min; (3)The step (2) in the resulting mixture is added to 1250ml10 C cold water, filtered The filter cake is too crude, the crude product was rinsed with 100ml water, then washed with water after the crude product was dissolved in 750ml of butyl acetate, 50 C incubation decolorization 30min. Filtered and allowed to stand, stratification, the upper organic layer (Product containing layer) 50 C, washed twice with water, water per 500ml. After washing to the water layer, The organic layer was distilled off under reduced pressure to 400ml of butyl acetate, allowed to stand for cooling to 15 C, the solid was filtered off with 50ml The resulting solid was rinsed with ethyl acetate, drained, placed in a vacuum drying oven at 50 C. L-ascorbic acid-6-palmitate was obtained as a white flake with a purity of 98. 1% and a yield of 91.3%.
  • 4
  • [ 623-65-4 ]
  • [ 108-24-7 ]
  • [ 137-66-6 ]
  • 2,5-di-O-acetyl-3,6-di-O-hexadecanoyl-L-ascorbic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.47 g Under argon atmosphere, 10 mL of DMSO was added to 3.00 g of 6-O-palmitoyl L-ascorbic acid and stirred, 1.61 g of triethylamine and 1.63 g of acetic anhydride were added while stirring, and the mixture was heated to 60 C. and stirred for 8 hours After that, it was extracted with ethyl acetate and washed with water. The extract was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography. Elution was performed with chloroform / methanol / water mixture (chloroform / methanol / water = 30/3 / 0.3 ? 10/3 / 0.3) and concentrated under reduced pressure to give 1.18 g of the first product (The step of obtaining the first product is referred to as reaction step 1).Triethylamine (0.26 g) and palmitic anhydride (1.29 g) were added while stirring, and the mixture was warmed to 60 C. and stirred for 3 hours , Extracted with ethyl acetate and washed with water. The extract was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the obtained residue was subjected to silica gel chromatography. Eluted with hexane / ethyl acetate mixture (hexane / ethyl acetate = 5/1 ? 1/1 ? 1/5) and concentrated under reduced pressure to give 0.47 g of the second product (first The step of obtaining the second product from the product is referred to as reaction step 2).
 

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