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79-83-4

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79-83-4 Usage

Physical properties

Pantothenic acid is composed of β-alanine joined to 2,4-dihydroxy-3,3- dimethylbutyric acid via an amide linkage. The molecule has an asymmetric center, and only the R-enantiomer, usually called D-(+)pantothenic acid, is biologically active and occurs naturally. Appearance: pantothenic acid is a yellow, viscous oil. Its calcium and other salts, however, are colorless crystalline substances; calcium pantothenate is the main product of commerce. Solubility: neither form is soluble in organic solvents, but each is soluble in water and ethanol. Stability: aqueous solu tions of pantothenic acid are unstable when heated under acidic or alkaline conditions

Originator

Panto-250 , Bio-Tech Pharmacal

Uses

Different sources of media describe the Uses of 79-83-4 differently. You can refer to the following data:
1. Pantothenic Acid is a member of the B complex vitamins; essential vitamin for the biosynthesis of coenzyme A in mammalian cells. Occurs ubiquitously in all animal and plant tissue. The richest common source is liver, but jelly of the queen bee contains 6 times as much as liver. Rice bran and molasses are other good sources.
2. Labelled Pantothenic Acid
3. Vitamin B5 is water-soluble. It is required for proper growth and maintenance of the body and is involved in body processes such as energy release from carbohydrates and metabolism of fatty acids. It is relatively stable through storage and is found in liver, eggs, and meat.

Manufacturing Process

Isobutylaldehyde reacted with formaldehyde in the presence potassium chromate as a result 2,2-dimethyl-3-hydroxy-propanal was obtained.The 2,2-dimethyl-3-hydroxy-propanal was treated by sodium cyanide so 2,4dihydroxy-3,3-dimethyl-butironitrile was prepared. The 2,4-dihydroxy-3,3-dimethyl-butironitrile was treated hydrochloric acid and D,L-3-hydroxy-4,4-dimethyl-dihydro-furan-2-one (D,L-pantolacton) was obtained. The racemic mixture of D- and L-pantolactons was a division of Dand L- isomers by the adding of α-phenylethylamine. So D-pantolacton was isolated. Acrylic acid contacted with NH3and β-alanine was obtained. D-Pantalacton reacted with β-alanine as a result 3-(2,4-dihydroxy-3,3dimethyl-butyrylamino)-propanoic acid was produced

Safety Profile

Moderately toxic by subcutaneous and intraperitoneal routes. When heated to decomposition it emits toxic vapors of NOx.

Check Digit Verification of cas no

The CAS Registry Mumber 79-83-4 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 9 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 79-83:
(4*7)+(3*9)+(2*8)+(1*3)=74
74 % 10 = 4
So 79-83-4 is a valid CAS Registry Number.
InChI:InChI=1/C9H17NO5/c1-9(2,5-11)7(14)8(15)10-4-3-6(12)13/h7,11,14H,3-5H2,1-2H3,(H,10,15)(H,12,13)/t7-/m0/s1

79-83-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name (R)-pantothenic acid

1.2 Other means of identification

Product number -
Other names kyselinapantothenova

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Skin Conditioning Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:79-83-4 SDS

79-83-4Synthetic route

calcium (R)-pantothenate
137-08-6

calcium (R)-pantothenate

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
With oxalic acid In water at 20℃; for 2h;95.11%
With (1S)-10-camphorsulfonic acid; trifluoroacetic acid at 0℃;
With Amberlite IR-120 In water Inert atmosphere;
With oxalic acid In water at 20℃; for 2h;
(R)-Pantolacton
599-04-2

(R)-Pantolacton

alkali salt of/the/ 3-amino-propionic acid

alkali salt of/the/ 3-amino-propionic acid

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
With water at 20℃;
With methanol at 20℃;
With isopropyl alcohol bei Siedetemperatur;
(R,E)-benzyl 3-(2,4-dihydroxy-3,3-dimethylbutanamido)acrylate
1265205-80-8

(R,E)-benzyl 3-(2,4-dihydroxy-3,3-dimethylbutanamido)acrylate

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol for 24h; Inert atmosphere;86%
DL-pantothenic acid

DL-pantothenic acid

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
With Cinchonidin
With Quinine
With quinine methohydroxide
With quinine methohydroxide
With Quinine
(R)-pantoate

(R)-pantoate

2-butenedioic acid
6915-18-0

2-butenedioic acid

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
With pantothenate synthetase; aspartate-α-decarboxylase; 3-methylaspartate ammonia lyase; ammonium chloride; ATP; magnesium chloride In aq. buffer at 25℃; for 24h; pH=9; Enzymatic reaction;70%
sodium salt of/the/ (R)-2.4-diacetoxy-3.3-dimethyl-butyric acid

sodium salt of/the/ (R)-2.4-diacetoxy-3.3-dimethyl-butyric acid

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
With thionyl chloride Umsetzung des gebildeten Saeurechlorids mit 3-Amino-propionsaeure-aethylester in Pyridin und Verseifung des Reaktionsprodukts mit aethanol.NaOH;
With thionyl chloride Umsetzung des gebildeten Saeurechlorids mit 3-Amino-propionsaeure-aethylester in Pyridin und Verseifung des Reaktionsprodukts mit wss.Ba(OH)2;
3-[(R)-2-(benzyloxy)-4-hydroxy-3,3-dimethylbutylamino]propanoic acid

3-[(R)-2-(benzyloxy)-4-hydroxy-3,3-dimethylbutylamino]propanoic acid

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol for 24h;92%
3-amino-propionic acid ethyl ester
924-73-2

3-amino-propionic acid ethyl ester

(-)(R)-pantolactone

(-)(R)-pantolactone

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
at 70℃; Hydrolyse des Reaktionsprodukts mit 0.5n-Ba(OH)2 bei 20grad;
at 70℃; Hydrolyse des Reaktionsprodukts mit 0.5n-Ba(OH)2 bei 20grad;
3-amino propanoic acid
107-95-9

3-amino propanoic acid

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
durch Escherichia coli;
durch Diphtherie-Bazillen;
durch verschiedene Hefen;
3-amino propanoic acid
107-95-9

3-amino propanoic acid

sodium salt of/the/ (+)(R)-2.4-dihydroxy-3.3-dimethyl-butyric acid

sodium salt of/the/ (+)(R)-2.4-dihydroxy-3.3-dimethyl-butyric acid

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
at 180℃;
N-formyl-(R)-2,2,5,5-tetramethyl-[1,3]dioxane-4-carboxylic acid amide

N-formyl-(R)-2,2,5,5-tetramethyl-[1,3]dioxane-4-carboxylic acid amide

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: benzene / 19 h / 95 °C / Inert atmosphere
2: bismuth(III) chloride / water; acetonitrile / 3 h / 20 °C / Inert atmosphere
3: palladium 10% on activated carbon; hydrogen / methanol / 24 h / Inert atmosphere
View Scheme
(R,E)-benzyl 3-(2,2,5,5-tetramethyl-1,3-dioxane-4-carboxamido)acrylate
1265205-79-5

(R,E)-benzyl 3-(2,2,5,5-tetramethyl-1,3-dioxane-4-carboxamido)acrylate

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: bismuth(III) chloride / water; acetonitrile / 3 h / 20 °C / Inert atmosphere
2: palladium 10% on activated carbon; hydrogen / methanol / 24 h / Inert atmosphere
View Scheme
(R)-2,4-Dihydroxy-3,3-dimethylbutyramide
27778-35-4

(R)-2,4-Dihydroxy-3,3-dimethylbutyramide

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: pyridinium p-toluenesulfonate / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / 0 °C / Inert atmosphere
2.2: 0 - 20 °C / Inert atmosphere
3.1: benzene / 19 h / 95 °C / Inert atmosphere
4.1: bismuth(III) chloride / water; acetonitrile / 3 h / 20 °C / Inert atmosphere
5.1: palladium 10% on activated carbon; hydrogen / methanol / 24 h / Inert atmosphere
View Scheme
(R)-Pantolacton
599-04-2

(R)-Pantolacton

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: ammonia / Inert atmosphere
2.1: pyridinium p-toluenesulfonate / Inert atmosphere
3.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / 0 °C / Inert atmosphere
3.2: 0 - 20 °C / Inert atmosphere
4.1: benzene / 19 h / 95 °C / Inert atmosphere
5.1: bismuth(III) chloride / water; acetonitrile / 3 h / 20 °C / Inert atmosphere
6.1: palladium 10% on activated carbon; hydrogen / methanol / 24 h / Inert atmosphere
View Scheme
(R)-2,2,5,5-Tetramethyl-1,3-dioxane-4-carboxamide
285141-00-6

(R)-2,2,5,5-Tetramethyl-1,3-dioxane-4-carboxamide

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / 0 °C / Inert atmosphere
1.2: 0 - 20 °C / Inert atmosphere
2.1: benzene / 19 h / 95 °C / Inert atmosphere
3.1: bismuth(III) chloride / water; acetonitrile / 3 h / 20 °C / Inert atmosphere
4.1: palladium 10% on activated carbon; hydrogen / methanol / 24 h / Inert atmosphere
View Scheme
pantothenic acid sodium salt
867-81-2

pantothenic acid sodium salt

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
With Amberlite IR-120 (H+-form) In water
With Dowex 50x8 (H+) In water
(R)-2,4-dihydroxy-3,3-dimethyl-N-(3-oxo-3-(prop-2-yn-1-ylamino)propyl)butanamide

(R)-2,4-dihydroxy-3,3-dimethyl-N-(3-oxo-3-(prop-2-yn-1-ylamino)propyl)butanamide

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
With pantetheinase; water Enzymatic reaction;
3-amino propanoic acid
107-95-9

3-amino propanoic acid

(+)(R)-2.4-dihydroxy-3.3-dimethyl-butyric acid-lactone

(+)(R)-2.4-dihydroxy-3.3-dimethyl-butyric acid-lactone

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
unter Einw. von Proteus morganii;
unter Einw. von Clostridium septicum;
unter Einw. von einem Stamm haemolytischer Streptococcen;
D-pantoic acid
1112-33-0

D-pantoic acid

3-amino propanoic acid
107-95-9

3-amino propanoic acid

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
unter Einw. von Proteus morganii;
unter Einw. von einem Stamm haemolytischer Streptococcen;
unter Einw. von Clostridium septicum;
(R)-Pantolacton
599-04-2

(R)-Pantolacton

3-amino propanoic acid
107-95-9

3-amino propanoic acid

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
With pantothenase UK-1 at 25℃; Equilibrium constant;
With 2-methoxy-ethanol; calcium
at 155 - 180℃;
pantothenol
81-13-0

pantothenol

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
With barium permanganate; sulfuric acid
im Organismus von Ratten;
(R)-3-(benzyloxy)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethylpropan-1-ol
895532-69-1

(R)-3-(benzyloxy)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethylpropan-1-ol

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: dmap; triethylamine / dichloromethane / 0 °C
1.2: 20 °C
2.1: acetic acid / 20 °C
3.1: sodium periodate / methanol; water
4.1: sodium dihydrogenphosphate; sodium chlorite / methanol; dichloromethane; water / 20 °C
5.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 °C
5.2: 16 h / 20 °C
6.1: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 3 h / 0 - 20 °C
7.1: palladium 10% on activated carbon; hydrogen / methanol / 24 h
View Scheme
(R)-3-(benzyloxy)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethylpropyl acetate
1377411-61-4

(R)-3-(benzyloxy)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethylpropyl acetate

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: acetic acid / 20 °C
2.1: sodium periodate / methanol; water
3.1: sodium dihydrogenphosphate; sodium chlorite / methanol; dichloromethane; water / 20 °C
4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 °C
4.2: 16 h / 20 °C
5.1: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 3 h / 0 - 20 °C
6.1: palladium 10% on activated carbon; hydrogen / methanol / 24 h
View Scheme
(3R,4R)-3-(benzyloxy)-4,5-dihydroxy-2,2-dimethylpentyl acetate
1377411-62-5

(3R,4R)-3-(benzyloxy)-4,5-dihydroxy-2,2-dimethylpentyl acetate

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium periodate / methanol; water
2.1: sodium dihydrogenphosphate; sodium chlorite / methanol; dichloromethane; water / 20 °C
3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 °C
3.2: 16 h / 20 °C
4.1: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 3 h / 0 - 20 °C
5.1: palladium 10% on activated carbon; hydrogen / methanol / 24 h
View Scheme
(R)-3-(benzyloxy)-2,2-dimethyl-4-oxobutyl acetate
1377411-63-6

(R)-3-(benzyloxy)-2,2-dimethyl-4-oxobutyl acetate

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium dihydrogenphosphate; sodium chlorite / methanol; dichloromethane; water / 20 °C
2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 °C
2.2: 16 h / 20 °C
3.1: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 3 h / 0 - 20 °C
4.1: palladium 10% on activated carbon; hydrogen / methanol / 24 h
View Scheme
(2R)-4-acetoxy-2-(benzyloxy)-3,3-dimethylbutanoic acid
1377411-64-7

(2R)-4-acetoxy-2-(benzyloxy)-3,3-dimethylbutanoic acid

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 °C
1.2: 16 h / 20 °C
2.1: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 3 h / 0 - 20 °C
3.1: palladium 10% on activated carbon; hydrogen / methanol / 24 h
View Scheme
methyl 3-[(R)-4-acetoxy-2-(benzyloxy)-3,3-dimethylbutanoylamino]propanoate
1377411-65-8

methyl 3-[(R)-4-acetoxy-2-(benzyloxy)-3,3-dimethylbutanoylamino]propanoate

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 3 h / 0 - 20 °C
2: palladium 10% on activated carbon; hydrogen / methanol / 24 h
View Scheme
ethyl 3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-2,2-dimethylpropanoate

ethyl 3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-2,2-dimethylpropanoate

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: Dess-Martin periodane / dichloromethane / 4 h / 20 °C
2.1: sodium tetrahydroborate / methanol / 1 h / -40 °C
3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 °C
3.2: 20 °C
4.1: lithium aluminium tetrahydride / diethyl ether / 0 °C
5.1: dmap; triethylamine / dichloromethane / 0 °C
5.2: 20 °C
6.1: acetic acid / 20 °C
7.1: sodium periodate / methanol; water
8.1: sodium dihydrogenphosphate; sodium chlorite / methanol; dichloromethane; water / 20 °C
9.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 °C
9.2: 16 h / 20 °C
10.1: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 3 h / 0 - 20 °C
11.1: palladium 10% on activated carbon; hydrogen / methanol / 24 h
View Scheme
(R)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-2,2-dimethylpropanoate
1377411-59-0

(R)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-2,2-dimethylpropanoate

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 °C
1.2: 20 °C
2.1: lithium aluminium tetrahydride / diethyl ether / 0 °C
3.1: dmap; triethylamine / dichloromethane / 0 °C
3.2: 20 °C
4.1: acetic acid / 20 °C
5.1: sodium periodate / methanol; water
6.1: sodium dihydrogenphosphate; sodium chlorite / methanol; dichloromethane; water / 20 °C
7.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 °C
7.2: 16 h / 20 °C
8.1: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 3 h / 0 - 20 °C
9.1: palladium 10% on activated carbon; hydrogen / methanol / 24 h
View Scheme
ethyl (R)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3-oxopropanoate
1377411-50-1

ethyl (R)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3-oxopropanoate

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: sodium tetrahydroborate / methanol / 1 h / -40 °C
2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 °C
2.2: 20 °C
3.1: lithium aluminium tetrahydride / diethyl ether / 0 °C
4.1: dmap; triethylamine / dichloromethane / 0 °C
4.2: 20 °C
5.1: acetic acid / 20 °C
6.1: sodium periodate / methanol; water
7.1: sodium dihydrogenphosphate; sodium chlorite / methanol; dichloromethane; water / 20 °C
8.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 °C
8.2: 16 h / 20 °C
9.1: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 3 h / 0 - 20 °C
10.1: palladium 10% on activated carbon; hydrogen / methanol / 24 h
View Scheme
pantothenic acid
79-83-4

pantothenic acid

acetic anhydride
108-24-7

acetic anhydride

N-[(2R)-2,4-diacetoxy-3,3-dimethylbutanoyl]-β-alanine
96199-41-6

N-[(2R)-2,4-diacetoxy-3,3-dimethylbutanoyl]-β-alanine

Conditions
ConditionsYield
With iodine at 0 - 20℃;97%
pantothenic acid
79-83-4

pantothenic acid

2-Methoxypropene
116-11-0

2-Methoxypropene

3-{[(4R)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl]carbonylamino}propionic acid
167308-62-5

3-{[(4R)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl]carbonylamino}propionic acid

Conditions
ConditionsYield
With toluene-4-sulfonic acid In acetone at 0 - 20℃; for 0.666667h;95%
With toluene-4-sulfonic acid In acetone at 0 - 20℃; for 0.75h; Inert atmosphere;
With toluene-4-sulfonic acid In acetone at 0 - 20℃; for 0.666667h;1.2 g
propylamine
107-10-8

propylamine

pantothenic acid
79-83-4

pantothenic acid

(R)-2,4-dihydroxy-3,3-dimethyl-N-(3-oxo-3-(propylamino)propyl)butanamide
874304-32-2

(R)-2,4-dihydroxy-3,3-dimethyl-N-(3-oxo-3-(propylamino)propyl)butanamide

Conditions
ConditionsYield
Stage #1: pantothenic acid With diphenyl phosphoryl azide; triethylamine In N,N-dimethyl-formamide at 0℃; for 0.333333h; Inert atmosphere;
Stage #2: propylamine In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;
79%
pantothenic acid
79-83-4

pantothenic acid

p-Anisaldehyde dimethyl acetal
2186-92-7

p-Anisaldehyde dimethyl acetal

3-{[(4R)-2-(p-methoxyphenyl)-5,5-dimethyl-1,3-dioxan-4-yl]carbonylamino}propionic acid
864239-47-4

3-{[(4R)-2-(p-methoxyphenyl)-5,5-dimethyl-1,3-dioxan-4-yl]carbonylamino}propionic acid

Conditions
ConditionsYield
With camphor-10-sulfonic acid In N,N-dimethyl-formamide at 20℃; for 16h;75%
With camphor-10-sulfonic acid In N,N-dimethyl-formamide68%
With (1S)-10-camphorsulfonic acid In dichloromethane at 20℃;51%
In dichloromethane at 20℃; for 8h;48%
With camphor-10-sulfonic acid In dichloromethane at 20℃;35%
pantothenic acid
79-83-4

pantothenic acid

N-(2-aminoethyl)-3-hydroxy-5,5-dimethoxy-3-methylpentanamide
101759-90-4

N-(2-aminoethyl)-3-hydroxy-5,5-dimethoxy-3-methylpentanamide

N-<3-<<(2,4-dihydroxy-3,3-dimethylbutanoyl)amino>propanamido>ethyl>-3-hydroxy-5,5-dimethoxy-3-methylpentanamide
101759-91-5, 101759-92-6

N-<3-<<(2,4-dihydroxy-3,3-dimethylbutanoyl)amino>propanamido>ethyl>-3-hydroxy-5,5-dimethoxy-3-methylpentanamide

Conditions
ConditionsYield
With 2,2'-dipyridyldisulphide; triphenylphosphine In N,N-dimethyl-formamide for 1h;71%
pantothenic acid
79-83-4

pantothenic acid

2-amino tritylthio ethane
1095-85-8

2-amino tritylthio ethane

S-tritylpantetheine

S-tritylpantetheine

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In acetonitrile at 20℃; for 24h;68%
pantothenic acid
79-83-4

pantothenic acid

2-amino tritylthio ethane
1095-85-8

2-amino tritylthio ethane

S-tritylpantetheine

S-tritylpantetheine

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In acetonitrile at 20℃; for 24h;68%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In acetonitrile at 20℃; for 24h;68%
pantothenic acid
79-83-4

pantothenic acid

p-anisaldehyde-dimethoxy-acetal

p-anisaldehyde-dimethoxy-acetal

3-{[2-(4-Methoxy-phenyl)-5,5-dimethyl-[1,3]dioxane-4-carbonyl]-amino}-propionic acid

3-{[2-(4-Methoxy-phenyl)-5,5-dimethyl-[1,3]dioxane-4-carbonyl]-amino}-propionic acid

Conditions
ConditionsYield
In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran51%
pantothenic acid
79-83-4

pantothenic acid

p-Anisaldehyde dimethyl acetal
2186-92-7

p-Anisaldehyde dimethyl acetal

C17H23NO6

C17H23NO6

Conditions
ConditionsYield
With camphor-10-sulfonic acid at 20℃; for 16h; Inert atmosphere;50%
pantothenic acid
79-83-4

pantothenic acid

thiophenol
108-98-5

thiophenol

S-phenyl thiopantothenate
142611-90-3

S-phenyl thiopantothenate

Conditions
ConditionsYield
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 2.16667h;48%
With diphenyl phosphoryl azide; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 3.16667h;42%
pantothenic acid
79-83-4

pantothenic acid

ethanethiol
75-08-1

ethanethiol

ethyl thiopantothenate
521981-75-9

ethyl thiopantothenate

Conditions
ConditionsYield
With diphenylphosphoranyl azide; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 2.33333h;46%
With diphenylphosphoranyl azide; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 2.16667h;32%
(2R)-2.4-dihydroxy-3.3-dimethyl-butyric acid-(3.4-dihydroxy-butylamide)

(2R)-2.4-dihydroxy-3.3-dimethyl-butyric acid-(3.4-dihydroxy-butylamide)

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
With barium permanganate; sulfuric acid
D-pantoic acid
1112-33-0

D-pantoic acid

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
unter Einw. von Acetobacter suboxydans;
coenzyme A
85-61-0

coenzyme A

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
Hydrolysis.enzymatische Hydrolyse;
L-valine
72-18-4

L-valine

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
Mechanism; multistep reaction; also by using (2RS)-(3S)-4-(13C)-valine; biosynthesis of pantothenic acid; stereospecificity of the biological hydroxymethylation of 2-oxo-isovaleric acid;
(+)(R)-2.4-dihydroxy-3.3-dimethyl-butyric acid-lactone

(+)(R)-2.4-dihydroxy-3.3-dimethyl-butyric acid-lactone

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
unter Einw. von Acetobacter suboxydans;
benzyl 3-aminopropionate
14529-00-1

benzyl 3-aminopropionate

(-)(R)-pantolactone

(-)(R)-pantolactone

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
at 100℃; Hydrogenolyse des Reaktionsprodukts an Platin in Eisessig oder Ameisensaeure;
pantothenol
81-13-0

pantothenol

sulfuric acid
7664-93-9

sulfuric acid

Ba(MnO4)2

Ba(MnO4)2

pantothenic acid
79-83-4

pantothenic acid

(R)-Pantolacton
599-04-2

(R)-Pantolacton

calcium-<3-amino propionate>

calcium-<3-amino propionate>

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
With methanol
(R)-2.4-diacetoxy-3.3-dimethyl-butyric acid-<3-hydroxy-propylamide>

(R)-2.4-diacetoxy-3.3-dimethyl-butyric acid-<3-hydroxy-propylamide>

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
With barium permanganate; sulfuric acid anschliessende Hydrolyse mit wss.Ba(OH)2;
(R)-2.4-dihydroxy-3.3-dimethyl-butyric acid-<3.3-diethoxy-propylamide>

(R)-2.4-dihydroxy-3.3-dimethyl-butyric acid-<3.3-diethoxy-propylamide>

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
With dihydrogen peroxide; oxalic acid
(R)-2.4-dihydroxy-3.3-dimethyl-butyric acid-<3-oxo-propylamide>

(R)-2.4-dihydroxy-3.3-dimethyl-butyric acid-<3-oxo-propylamide>

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
With barium dihydroxide; silver(l) oxide
sodium β-alaninate
16690-93-0

sodium β-alaninate

(R)-2.4-dihydroxy-3.3-dimethyl-butyric acid amide

(R)-2.4-dihydroxy-3.3-dimethyl-butyric acid amide

pantothenic acid
79-83-4

pantothenic acid

Conditions
ConditionsYield
at 100℃;
oxalic acid
144-62-7

oxalic acid

(R)-N-(3,3-diethoxypropyl)-2,4-dihydroxy-3,3-dimethylbutanamide
851986-98-6

(R)-N-(3,3-diethoxypropyl)-2,4-dihydroxy-3,3-dimethylbutanamide

H2O2

H2O2

water

water

pantothenic acid
79-83-4

pantothenic acid

pantothenic acid
79-83-4

pantothenic acid

dicyclohexyl-carbodiimide
538-75-0

dicyclohexyl-carbodiimide

N-(D-Pantothenoyl)-N,N'-dicyclohexylurea
75980-10-8

N-(D-Pantothenoyl)-N,N'-dicyclohexylurea

Conditions
ConditionsYield
In 1,4-dioxane for 24h;42.3%
pantothenic acid
79-83-4

pantothenic acid

sodium thiomethoxide
5188-07-8

sodium thiomethoxide

methyl thiopantothenate

methyl thiopantothenate

Conditions
ConditionsYield
With diphenylphosphoranyl azide; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 2.16667h;39%
pantothenic acid
79-83-4

pantothenic acid

Propargylamine
2450-71-7

Propargylamine

(R)-2,4-dihydroxy-3,3-dimethyl-N-(3-oxo-3-(prop-2-yn-1-ylamino)propyl)butanamide

(R)-2,4-dihydroxy-3,3-dimethyl-N-(3-oxo-3-(prop-2-yn-1-ylamino)propyl)butanamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide38%
ethanol
64-17-5

ethanol

pantothenic acid
79-83-4

pantothenic acid

ethyl D-pantothenate
10527-68-1

ethyl D-pantothenate

Conditions
ConditionsYield
With hydrogenchloride33%
3-ethylhexane
619-99-8

3-ethylhexane

pantothenic acid
79-83-4

pantothenic acid

[2-(2,6-Dichloro-phenylamino)-phenyl]-acetic acid 2-amino-ethyl ester

[2-(2,6-Dichloro-phenylamino)-phenyl]-acetic acid 2-amino-ethyl ester

4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran
96042-30-7

4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran

[2-(2,6-Dichloro-phenylamino)-phenyl]-acetic acid 2-[3-((R)-2,4-dihydroxy-3,3-dimethyl-butyrylamino)-propionylamino]-ethyl ester

[2-(2,6-Dichloro-phenylamino)-phenyl]-acetic acid 2-[3-((R)-2,4-dihydroxy-3,3-dimethyl-butyrylamino)-propionylamino]-ethyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; triethylamine In methanol; N,N-dimethyl-formamide26.4%
pantothenic acid
79-83-4

pantothenic acid

(2-aminoethyl)methylsulfide
18542-42-2

(2-aminoethyl)methylsulfide

(R)-2,4-dihydroxy-3,3-dimethyl-N-(3-((2-(methylthio)ethyl)amino)-3-oxopropyl)butanamide

(R)-2,4-dihydroxy-3,3-dimethyl-N-(3-((2-(methylthio)ethyl)amino)-3-oxopropyl)butanamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 2h;21.02%

79-83-4Relevant articles and documents

McBurney,Bollen,Williams

, p. 301 (1935)

-

Mueller,Klotz

, p. 3086 (1938)

-

-

Weinstock et al.

, p. 1421,1424 (1939)

-

Chemical Proteomic Profiling of Protein 4′-Phosphopantetheinylation in Mammalian Cells

Chen, Nan,Li, Yuanpei,Liu, Yuan,Wang, Chu

supporting information, p. 16069 - 16075 (2020/07/21)

Protein 4′-phosphopantetheinylation is an essential post-translational modification (PTM) in prokaryotes and eukaryotes. So far, only five protein substrates of this specific PTM have been discovered in mammalian cells. These proteins are known to perform important functions, including fatty acid biosynthesis and folate metabolism, as well as β-alanine activation. To explore existing and new substrates of 4′-phosphopantetheinylation in mammalian proteomes, we designed and synthesized a series of new pantetheine analogue probes, enabling effective metabolic labelling of 4′-phosphopantetheinylated proteins in HepG2 cells. In combination with a quantitative chemical proteomic platform, we enriched and identified all the currently known 4′-phosphopantetheinylated proteins with high confidence, and unambiguously determined their exact sites of modification. More encouragingly, we discovered, using targeted chemical proteomics, a potential 4′-phosphopantetheinylation site in the protein of mitochondrial dehydrogenase/reductase SDR family member 2 (DHRS2).

PANTETHEINE DERIVATIVES AND USES THEREOF

-

Paragraph 2065, (2020/06/19)

The present disclosure relates to compounds of Formula (I), (II), or (II'): (I), (II), (II'), and pharmaceutically acceptable salts or solvates thereof. The present disclosure also relates to pharmaceutical compositions comprising the compounds and therapeutic and diagnostic uses of the compounds and pharmaceutical compositions.

Probing the ligand preferences of the three types of bacterial pantothenate kinase

Guan, Jinming,Barnard, Leanne,Cresson, Jeanne,Hoegl, Annabelle,Chang, Justin H.,Strauss, Erick,Auclair, Karine

supporting information, p. 5896 - 5902 (2018/11/23)

Pantothenate kinase (PanK) catalyzes the transformation of pantothenate to 4′-phosphopantothenate, the first committed step in coenzyme A biosynthesis. While numerous pantothenate antimetabolites and PanK inhibitors have been reported for bacterial type I and type II PanKs, only a few weak inhibitors are known for bacterial type III PanK enzymes. Here, a series of pantothenate analogues were synthesized using convenient synthetic methodology. The compounds were exploited as small organic probes to compare the ligand preferences of the three different types of bacterial PanK. Overall, several new inhibitors and substrates were identified for each type of PanK.

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