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[ CAS No. 137-66-6 ] {[proInfo.proName]}

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Chemical Structure| 137-66-6
Chemical Structure| 137-66-6
Structure of 137-66-6 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 137-66-6 ]

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Product Details of [ 137-66-6 ]

CAS No. :137-66-6 MDL No. :MFCD00005377
Formula : C22H38O7 Boiling Point : -
Linear Structure Formula :- InChI Key :QAQJMLQRFWZOBN-LAUBAEHRSA-N
M.W : 414.53 Pubchem ID :54680660
Synonyms :
L-Ascorbic acid 6-hexadecanoate;6-O-Palmitoyl-L-ascorbic acid;HSDB 418;CCRIS 3930;BRN 0096552;6-Palmitoylascorbic acid;Vitamin C palmitate;NSC 402451;Ascorbylpalmitic Acid
Chemical Name :(S)-2-((R)-3,4-Dihydroxy-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl palmitate

Calculated chemistry of [ 137-66-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 29
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.82
Num. rotatable bonds : 18
Num. H-bond acceptors : 7.0
Num. H-bond donors : 3.0
Molar Refractivity : 112.16
TPSA : 113.29 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.38 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.26
Log Po/w (XLOGP3) : 6.26
Log Po/w (WLOGP) : 4.62
Log Po/w (MLOGP) : 1.62
Log Po/w (SILICOS-IT) : 4.86
Consensus Log Po/w : 4.32

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 1.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -5.17
Solubility : 0.00283 mg/ml ; 0.00000682 mol/l
Class : Moderately soluble
Log S (Ali) : -8.43
Solubility : 0.00000155 mg/ml ; 0.0000000038 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -4.74
Solubility : 0.00756 mg/ml ; 0.0000182 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 5.12

Safety of [ 137-66-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 137-66-6 ]

* 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 [ 137-66-6 ]

[ 137-66-6 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 57-10-3 ]
  • [ 50-81-7 ]
  • [ 137-66-6 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; at 18 - 35℃;Inert atmosphere; (1) 100 ml (about 184 g) 99-99.5% sulfuric acid was added to 250 ml four-neck flask with stirring, 35 g of palmitic acid was added at 30-35C dissolved with stirring for 0.5-1 hour. The temperature was dropped to 20-25C under protection of nitrogen, 17.6 grams of vitamin C was added with stirring, and stirring was stopped until completely dissolved, and insulated at 18-20C for 48 hours to obtain reaction liquid vitamin C palmitate. (2) The temperature was controlled to below 40C , the reaction solution was slowly poured into 200 ml 4-neck flask placed in ice-bath containing 200 ml cooling water. 700 ml of toluene was added and then subjected to extraction, heated to 60C and cooled naturally with stirring, when the temperature of the system was reduced to about 40C, stratified, and lower waste acid was separated leaving the toluene layer. (3) To the toluene layer 30-35 200 ml of water was added, stirred at 30-35C for 3 hours, crystallized at 30-35C for three hours, cooled in ice-water at 10-15C, stirred for one hour and filtered. The filter cake was washed with 50 ml of toluene, and then washed with 500 ml of water at 30-35C. (4) The filter cake was added to 500 ml water at 30-35C for 1 hour, filtered, and then washed with 200 ml water at 30-35C and the effluent water PH =7 was drained, discharged, and air-dried at room temperature for one day to constant weight. The crude product of vitamin C palmitate 33-34 g was obtained. Yield of 79.7-82.1%. (5) Take the above crude vitamin C palmitate, dissolved in 7.5 times the volume of 95% ethanol at 35-40 deg. C, filtered, washed with 0.5 volume of 95% ethanol and filtrate had crystallized, heated at 35-40C until fully dissolved and transferred to 500 ml 4-neck flask, rapidly cooled to -25--20C, crystallized by stirring for 3 hours, filtered, the filter cake was washed with 95% cold ethanol and vacuum-dried at 40-50C for 8 hours to obtain 30-31 g of product. Yield 90-92%.
  • 2
  • [ 693-38-9 ]
  • [ 50-81-7 ]
  • [ 137-66-6 ]
  • 3
  • [ 107-02-8 ]
  • [ 137-66-6 ]
  • [ 121850-68-8 ]
  • 6
  • [ 67-63-0 ]
  • [ 107-02-8 ]
  • [ 137-66-6 ]
  • Hexadecanoic acid (R)-2-hydroxy-2-((5S,8R)-2-isopropoxy-6,9-dioxo-1,7-dioxa-spiro[4.4]non-8-yl)-ethyl ester [ No CAS ]
  • 7
  • [ 67-56-1 ]
  • [ 107-02-8 ]
  • [ 137-66-6 ]
  • Hexadecanoic acid (R)-2-((4aS,7R,7aR)-2,4a-dihydroxy-7a-methoxy-5-oxo-hexahydro-furo[3,4-b]pyran-7-yl)-2-hydroxy-ethyl ester [ No CAS ]
  • 8
  • [ 137-66-6 ]
  • [ 63247-05-2 ]
  • 10
  • [ 107-02-8 ]
  • [ 137-66-6 ]
  • Hexadecanoic acid (S)-2-hydroxy-2-[(2R,4S)-4-hydroxy-3,5-dioxo-4-(3-oxo-propyl)-tetrahydro-furan-2-yl]-ethyl ester [ No CAS ]
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