867-81-2

Basic information

• Product Name: Sodium D-pantothenate
• Synonyms: (r)-n-(2,4-dihydroxy-3,3-dimethyl-1-oxobutyl)-beta-alanine monosodium salt;SODIUM D-PANTOTHENATE;SODIUM PANTHOTENATE;SODIUM PANTOTHENATE;beta-alanine,n-(2,4-dihydroxy-3,3-dimethyl-1-oxobutyl)-,monosodiumsalt,(t;heta)-;monosodiumsalt,d-pantothenicaci;N-(2,4-dihydroxy-3,3-dimethyl-1-oxobutyl)-,monosodiumsalt,(R)-.beta.-Alanine
• CAS NO: 867-81-2
• Molecular Formula: C₉H₁₆NO₅*Na
• Molecular Weight: 241.22
• EINECS: 212-768-6
• Product Categories: Biochemistry;Vitamins;Vitamins and derivatives;API
• Mol File: 867-81-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: 171-178 °C(lit.)
• Boiling Point: 551.5 °C at 760 mmHg
• Flash Point: 287.3 °C
• Appearance: /
• Refractive Index: 27 ° (C=5, H2O)
• Storage Temp.: 2-8°C
• Solubility: Water (Slightly)
• CAS DataBase Reference: Sodium D-pantothenate(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium D-pantothenate(867-81-2)
• EPA Substance Registry System: Sodium D-pantothenate(867-81-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-48-41-37/38-20/21/22
• Safety Statements: 26-36-45-36/37/39-22-24/25
• Hazardous Substances Data: 867-81-2(Hazardous Substances Data)

Usage

Description

Sodium D-pantothenate is the sodium salt of the biological active enantiomer of pantothenic acid (vitamin B5). As D-pantothenic acid is a precursor in the biosynthesis of coenzyme A, sodium D- pantothenate is used in the synthesis of coenzyme A. It is also used in foods as a dietary supplement.

References

[1] George A. Burdock, Encyclopedia of Food and Color Additives, volume 3, 1996

Purification Methods

Crystallise the salt from absolute EtOH. It is very hygroscopic (keep in sealed ampoules). The free acid is a viscous hygroscopic oil with [] 25D +37.5o (c 5, H2O), easily destroyed by acids and bases. [Beilstein 4 IV 2569.]

InChI:InChI=1/C9H17NO5.Na/c1-9(2,15)5-6(11)8(14)10-4-3-7(12)13;/h6,11,15H,3-5H2,1-2H3,(H,10,14)(H,12,13);/q;+1/p-1/t6-;/m1./s1

Synthetic route

sodium β-alaninate (16690-93-0) + (R)-Pantolacton (599-04-2) → pantothenic acid sodium salt (867-81-2)

Conditions	Yield
In ethanol for 3h; Reflux;	76.3 g

pantothenic acid sodium salt (867-81-2) + 2,2-dimethoxy-propane (77-76-9) → 3-{[(4R)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl]carbonylamino}propionic acid (167308-62-5)

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 20℃; for 12h;	100%

3,3-dimethyl-4-(tetrahydropyran-2-yloxy)butylamine (616236-11-4) + pantothenic acid sodium salt (867-81-2) → (2R)-N-{2-[3,3-dimethyl-4-(tetrahydropyran-2-yloxy)butylcarbamoyl]ethyl}-2,4-dihydroxy-3,3-dimethylbutyramide (616236-12-5)

Conditions	Yield
With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 20℃;	56%

(E)-5-aminopent-2-enoate trifluoroacetate salt (1256165-05-5) + pantothenic acid sodium salt (867-81-2) → ethyl (R,E)-5-(3-(2,4-dihydroxy-3,3-dimethylbutanamido)propanamido)pent-2-enoate (1245941-16-5)

Conditions	Yield
With N-ethylmorpholine;; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃;	41%

[2H9]-trimethylchlorosilane (20395-57-7) + pantothenic acid sodium salt (867-81-2) → tris([2H9]trimethylsilyl)-(R)-pantothenic acid

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃; for 8h;

N-methyl-N-tert-butyldimethylsilyl-1,1,1-trifluoroacetamide (77377-52-7) + pantothenic acid sodium salt (867-81-2) → tris(tert-butyldimethylsilyl)pantothenic acid

Conditions	Yield
With pyridine at 80℃; for 1h;

diethyl cyanophosphonate (2942-58-7) + pantothenic acid sodium salt (867-81-2) + 1-amino-2-propene (107-11-9) → pantothenic acid allyl amide

Conditions	Yield
With concentrated aqueous HCl; triethylamine In water; ethyl acetate	8.03 g (75%)

pantothenic acid sodium salt (867-81-2) → pantothenic acid (79-83-4)

Conditions	Yield
With Amberlite IR-120 (H+-form) In water
With Dowex 50x8 (H+) In water

pantothenic acid sodium salt (867-81-2) → amino(dethia)pantetheine acetonide

Conditions	Yield
Multi-step reaction with 2 steps 1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 12 h / 20 °C 2.1: chloroformic acid ethyl ester; triethylamine / dichloromethane / 0.25 h / 4 °C 2.2: 12 h / 20 °C View Scheme

pantothenic acid sodium salt (867-81-2) → 2-bromopropionyloxa(dethia)pantetheine acetonide

Conditions	Yield
Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 12 h / 20 °C 2.1: chloroformic acid ethyl ester; triethylamine / dichloromethane / 0.25 h / 4 °C 2.2: 12 h / 20 °C 3.1: pyridine / dichloromethane / 12 h / 4 - 20 °C View Scheme

pantothenic acid sodium salt (867-81-2) → 2-bromopropionylamino(dethia)pantetheine acetonide

Conditions	Yield
Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 12 h / 20 °C 2.1: chloroformic acid ethyl ester; triethylamine / dichloromethane / 0.25 h / 4 °C 2.2: 12 h / 20 °C 3.1: pyridine / dichloromethane / 12 h / 4 - 20 °C View Scheme

pantothenic acid sodium salt (867-81-2) → 2-sulfinatepropionyloxa(dethia)pantetheine acetonide

Conditions	Yield
Multi-step reaction with 4 steps 1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 12 h / 20 °C 2.1: chloroformic acid ethyl ester; triethylamine / dichloromethane / 0.25 h / 4 °C 2.2: 12 h / 20 °C 3.1: pyridine / dichloromethane / 12 h / 4 - 20 °C 4.1: sodium hydrogencarbonate; sodium dithionite / water / 0.5 h / 20 °C View Scheme

pantothenic acid sodium salt (867-81-2) → 2-sulfinatepropionylamino(dethia)pantetheine acetonide

Conditions	Yield
Multi-step reaction with 4 steps 1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 12 h / 20 °C 2.1: chloroformic acid ethyl ester; triethylamine / dichloromethane / 0.25 h / 4 °C 2.2: 12 h / 20 °C 3.1: pyridine / dichloromethane / 12 h / 4 - 20 °C 4.1: sodium hydrogencarbonate; sodium dithionite / water / 0.5 h / 20 °C View Scheme

pantothenic acid sodium salt (867-81-2) → 2-sulfonatepropionyloxa(dethia)pantetheine

Conditions	Yield
Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 12 h / 20 °C 2.1: chloroformic acid ethyl ester; triethylamine / dichloromethane / 0.25 h / 4 °C 2.2: 12 h / 20 °C 3.1: pyridine / dichloromethane / 12 h / 4 - 20 °C 4.1: sodium hydrogencarbonate; sodium dithionite / water / 0.5 h / 20 °C 5.1: oxygen / water / 18 h / 20 °C 5.2: 20 °C View Scheme

pantothenic acid sodium salt (867-81-2) → 2-sulfonatepropionylamino(dethia)pantetheine

Conditions	Yield
Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 12 h / 20 °C 2.1: chloroformic acid ethyl ester; triethylamine / dichloromethane / 0.25 h / 4 °C 2.2: 12 h / 20 °C 3.1: pyridine / dichloromethane / 12 h / 4 - 20 °C 4.1: sodium hydrogencarbonate; sodium dithionite / water / 0.5 h / 20 °C 5.1: oxygen / water / 18 h / 20 °C 5.2: 20 °C View Scheme

pantothenic acid sodium salt (867-81-2) → 2-nitropropionyloxa(dethia)pantetheine acetonide

Conditions	Yield
Multi-step reaction with 4 steps 1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 12 h / 20 °C 2.1: chloroformic acid ethyl ester; triethylamine / dichloromethane / 0.25 h / 4 °C 2.2: 12 h / 20 °C 3.1: pyridine / dichloromethane / 12 h / 4 - 20 °C 4.1: 3,5-dihydroxyphenol; potassium nitrite / N,N-dimethyl-formamide / 12 h / 20 °C View Scheme

pantothenic acid sodium salt (867-81-2) → 2-nitropropionylamino(dethia)pantetheine acetonide

Conditions	Yield
Multi-step reaction with 4 steps 1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 12 h / 20 °C 2.1: chloroformic acid ethyl ester; triethylamine / dichloromethane / 0.25 h / 4 °C 2.2: 12 h / 20 °C 3.1: pyridine / dichloromethane / 12 h / 4 - 20 °C 4.1: 3,5-dihydroxyphenol; potassium nitrite / N,N-dimethyl-formamide / 12 h / 20 °C View Scheme

pantothenic acid sodium salt (867-81-2) → 2-nitropropionyloxa(dethia)pantetheine

Conditions	Yield
Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 12 h / 20 °C 2.1: chloroformic acid ethyl ester; triethylamine / dichloromethane / 0.25 h / 4 °C 2.2: 12 h / 20 °C 3.1: pyridine / dichloromethane / 12 h / 4 - 20 °C 4.1: 3,5-dihydroxyphenol; potassium nitrite / N,N-dimethyl-formamide / 12 h / 20 °C 5.1: trifluoroacetic acid / water / 20 °C View Scheme

pantothenic acid sodium salt (867-81-2) → 2-nitropropionylamino(dethia)pantetheine

Conditions	Yield
Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 12 h / 20 °C 2.1: chloroformic acid ethyl ester; triethylamine / dichloromethane / 0.25 h / 4 °C 2.2: 12 h / 20 °C 3.1: pyridine / dichloromethane / 12 h / 4 - 20 °C 4.1: 3,5-dihydroxyphenol; potassium nitrite / N,N-dimethyl-formamide / 12 h / 20 °C 5.1: trifluoroacetic acid / water / 20 °C View Scheme

pantothenic acid sodium salt (867-81-2) → C14H24N2O12PS(3-)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 12 h / 20 °C 2.1: chloroformic acid ethyl ester; triethylamine / dichloromethane / 0.25 h / 4 °C 2.2: 12 h / 20 °C 3.1: pyridine / dichloromethane / 12 h / 4 - 20 °C 4.1: sodium hydrogencarbonate; sodium dithionite / water / 0.5 h / 20 °C 5.1: oxygen / water / 18 h / 20 °C 5.2: 20 °C 6.1: ATP; recombinant enzym pJLHis6T-ecCoaA; magnesium chloride; sodium chloride / aq. buffer / 2 h / 20 °C / Enzymatic reaction View Scheme

pantothenic acid sodium salt (867-81-2) → 2-sulfonatepropionyloxa(dethia)CoA

Conditions

Yield

Multi-step reaction with 7 steps 1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 12 h / 20 °C 2.1: chloroformic acid ethyl ester; triethylamine / dichloromethane / 0.25 h / 4 °C 2.2: 12 h / 20 °C 3.1: pyridine / dichloromethane / 12 h / 4 - 20 °C 4.1: sodium hydrogencarbonate; sodium dithionite / water / 0.5 h / 20 °C 5.1: oxygen / water / 18 h / 20 °C 5.2: 20 °C 6.1: ATP; recombinant enzym pJLHis6T-ecCoaA; magnesium chloride; sodium chloride / aq. buffer / 2 h / 20 °C / Enzymatic reaction 7.1: recombinant enzym pJLHis6T-ecCoaD; magnesium chloride; sodium chloride / aq. buffer / 2 h / 20 °C / pH 8 / Enzymatic reaction 7.2: 3407 / 20 °C / pH 8 / Enzymatic reaction View Scheme

pantothenic acid sodium salt (867-81-2) → C14H25N3O11PS(3-)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 12 h / 20 °C 2.1: chloroformic acid ethyl ester; triethylamine / dichloromethane / 0.25 h / 4 °C 2.2: 12 h / 20 °C 3.1: pyridine / dichloromethane / 12 h / 4 - 20 °C 4.1: sodium hydrogencarbonate; sodium dithionite / water / 0.5 h / 20 °C 5.1: oxygen / water / 18 h / 20 °C 5.2: 20 °C 6.1: ATP; recombinant enzym pJLHis6T-ecCoaA; magnesium chloride; sodium chloride / aq. buffer / 2 h / 20 °C / Enzymatic reaction View Scheme

pantothenic acid sodium salt (867-81-2) → 2-sulfonatepropionylamino(dethia)CoA

Conditions

Yield

Multi-step reaction with 7 steps 1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 12 h / 20 °C 2.1: chloroformic acid ethyl ester; triethylamine / dichloromethane / 0.25 h / 4 °C 2.2: 12 h / 20 °C 3.1: pyridine / dichloromethane / 12 h / 4 - 20 °C 4.1: sodium hydrogencarbonate; sodium dithionite / water / 0.5 h / 20 °C 5.1: oxygen / water / 18 h / 20 °C 5.2: 20 °C 6.1: ATP; recombinant enzym pJLHis6T-ecCoaA; magnesium chloride; sodium chloride / aq. buffer / 2 h / 20 °C / Enzymatic reaction 7.1: recombinant enzym pJLHis6T-ecCoaD; magnesium chloride; sodium chloride / aq. buffer / 2 h / 20 °C / pH 8 / Enzymatic reaction 7.2: 3407 / 20 °C / pH 8 / Enzymatic reaction View Scheme

pantothenic acid sodium salt (867-81-2) → C14H24N3O11P(2-)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 12 h / 20 °C 2.1: chloroformic acid ethyl ester; triethylamine / dichloromethane / 0.25 h / 4 °C 2.2: 12 h / 20 °C 3.1: pyridine / dichloromethane / 12 h / 4 - 20 °C 4.1: 3,5-dihydroxyphenol; potassium nitrite / N,N-dimethyl-formamide / 12 h / 20 °C 5.1: trifluoroacetic acid / water / 20 °C 6.1: ATP; recombinant enzym pJLHis6T-ecCoaA; magnesium chloride; sodium chloride / aq. buffer / 2 h / 20 °C / Enzymatic reaction View Scheme

pantothenic acid sodium salt (867-81-2) → 2-nitropropionyloxa(dethia)CoA

Conditions

Yield

Multi-step reaction with 7 steps 1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 12 h / 20 °C 2.1: chloroformic acid ethyl ester; triethylamine / dichloromethane / 0.25 h / 4 °C 2.2: 12 h / 20 °C 3.1: pyridine / dichloromethane / 12 h / 4 - 20 °C 4.1: 3,5-dihydroxyphenol; potassium nitrite / N,N-dimethyl-formamide / 12 h / 20 °C 5.1: trifluoroacetic acid / water / 20 °C 6.1: ATP; recombinant enzym pJLHis6T-ecCoaA; magnesium chloride; sodium chloride / aq. buffer / 2 h / 20 °C / Enzymatic reaction 7.1: recombinant enzym pJLHis6T-ecCoaD; magnesium chloride; sodium chloride / aq. buffer / 2 h / 20 °C / pH 8 / Enzymatic reaction 7.2: 3407 / 20 °C / pH 8 / Enzymatic reaction View Scheme

pantothenic acid sodium salt (867-81-2) → C14H25N4O10P(2-)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 12 h / 20 °C 2.1: chloroformic acid ethyl ester; triethylamine / dichloromethane / 0.25 h / 4 °C 2.2: 12 h / 20 °C 3.1: pyridine / dichloromethane / 12 h / 4 - 20 °C 4.1: 3,5-dihydroxyphenol; potassium nitrite / N,N-dimethyl-formamide / 12 h / 20 °C 5.1: trifluoroacetic acid / water / 20 °C 6.1: ATP; recombinant enzym pJLHis6T-ecCoaA; magnesium chloride; sodium chloride / aq. buffer / 2 h / 20 °C / Enzymatic reaction View Scheme

pantothenic acid sodium salt (867-81-2) → 2-nitropropionylamino(dethia)CoA

Conditions

Yield

Multi-step reaction with 7 steps 1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 12 h / 20 °C 2.1: chloroformic acid ethyl ester; triethylamine / dichloromethane / 0.25 h / 4 °C 2.2: 12 h / 20 °C 3.1: pyridine / dichloromethane / 12 h / 4 - 20 °C 4.1: 3,5-dihydroxyphenol; potassium nitrite / N,N-dimethyl-formamide / 12 h / 20 °C 5.1: trifluoroacetic acid / water / 20 °C 6.1: ATP; recombinant enzym pJLHis6T-ecCoaA; magnesium chloride; sodium chloride / aq. buffer / 2 h / 20 °C / Enzymatic reaction 7.1: recombinant enzym pJLHis6T-ecCoaD; magnesium chloride; sodium chloride / aq. buffer / 2 h / 20 °C / pH 8 / Enzymatic reaction 7.2: 3407 / 20 °C / pH 8 / Enzymatic reaction View Scheme

pantothenic acid sodium salt (867-81-2) → (4R)-N-(3-[(2-hydroxyethyl)amino]-3-oxopropyl)-2,2,5,5-tetramethyl-1,3-dioxane-4-carboxamide (1217509-11-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 12 h / 20 °C 2.1: chloroformic acid ethyl ester; triethylamine / dichloromethane / 0.25 h / 4 °C 2.2: 12 h / 20 °C View Scheme

Upstream product

• 16690-93-0 sodium β-alaninate 
• 599-04-2 (R)-Pantolacton 

Downstream Products

• 79-83-4 pantothenic acid 

Relevant articles and documents

D - Pantothenic acid sodium crystal and its preparation and use (by machine translation)

The invention belongs to the field of chemical medicine, in particular to D - Pantothenic acid sodium crystal and its preparation and use. The invention provides a D - Pantothenic acid sodium crystal, the crystal in the D - Pantothenic acid sodium 2 θ expressed on the X - ray powder diffraction spectrum, in 10.75 ± 0.20 °, 16 . 09 ± 0.20 °, 17 . 86 ± 0.20 °, 18 . 36 ± 0.20 °, 19 . 54 ± 0.20 °, 20 . 11 ± 0.20 °, 24 . 62 ± 0.20 °, 25 . 93 ± 0.20 °, 27 . 24 ± 0.20 °, 27 . 72 ± 0.20 °, 29 . 52 ± 0.20 °, 31 . 16 ± 0.20 ° and 39.65 ± 0.20 ° has a characteristic diffraction peak; in differential scanning thermal analysis on the Atlas, the D - Pantothenic acid sodium crystal in the 168 °C has caused by crystal melting endothermic peak; through the melting point determination, said D - Pantothenic acid sodium crystal melting point 166 - 170 °C. The invention also provides the above-mentioned D - Pantothenic acid sodium crystal preparation method and use. The invention provides D - Pantothenic acid sodium crystal in the air low hygroscopicity, high stability, so and can store and use more long time, prolonging the shelf life of the product. (by machine translation)