79-50-5

Basic information

• Product Name: DL-Pantolactone
• Synonyms: Pantoicacid-lactone;2(3H)-Furanone, dihydro-3-hydroxy-4,4-dimethyl-, (+-)-;DL-alpha-Hydroxy-beta,beta-dimethyl-alpha-butyrolactone;DL-γ-butyrolactone;DL-PANTOYL LACTONE 97%;Dihydro-3-hydroxy-4H-dimethyl-2[3H]-furanone;dl-α-hydroxy-β,β-dimethyl-γ-butyrolactone;β,β-dimethyl-α-hydroxy-γ-butyrolactone
• CAS NO: 79-50-5
• Molecular Formula: C₆H₁₀O₃
• Molecular Weight: 130.14
• EINECS: 201-210-7
• Product Categories: Pharmaceutical Intermediates
• Mol File: 79-50-5.mol
• Article Data: 120

Chemical Properties

• Melting Point: 74-78 °C(lit.)
• Boiling Point: 121°C/11mmHg(lit.)
• Flash Point: 122℃
• Appearance: /
• Density: 1.165 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: H2O: soluble1g/10 mL, clear, colorless to almost colorless
• PKA: 13.12±0.40(Predicted)
• Stability: Unstable in Aqueous Solution
• BRN: 80958
• CAS DataBase Reference: DL-Pantolactone(CAS DataBase Reference)
• NIST Chemistry Reference: DL-Pantolactone(79-50-5)
• EPA Substance Registry System: DL-Pantolactone(79-50-5)

Safety Data

• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26
• WGK Germany: 3
• F: 3-10-21
• Hazardous Substances Data: 79-50-5(Hazardous Substances Data)

Usage

Uses

DL-α-Hydroxy-β,β-dimethyl-γ-butyrolactone (DL-pantolactone) may be used in the preparation of 3,5-dinitrobenzoyl-DL-pantolactone.

Synthesis Reference(s)

Journal of the American Chemical Society, 79, p. 3545, 1957 DOI: 10.1021/ja01570a064

InChI:InChI=1/C6H10O3/c1-6(2)3-9-5(8)4(6)7/h4,7H,3H2,1-2H3

Synthetic route

calcium-N-(2,4-dihydroxy-3,3-dimethylbutyryl)-β-alaninate (137-08-6, 867-80-1, 6381-62-0, 6381-63-1, 15773-29-2, 64789-49-7, 122484-60-0, 131346-21-9) → pantolactone (79-50-5) + 3-amino propanoic acid (107-95-9)

Conditions	Yield
With hydrogenchloride In water at 80℃; for 1.75h; Rate constant;	A 100% B 100%

pantothenic acid sodium salt (75033-16-8) → pantolactone (79-50-5) + 3-amino propanoic acid (107-95-9)

Conditions	Yield
With hydrogenchloride In water at 80℃; for 1.25h; Rate constant;	A 100% B 100%

ketopantolactone (13031-04-4) → pantolactone (79-50-5)

Conditions	Yield
With hydrogen; Et4N	99%
With F6P(1-)*C20H36IrN6P2(1+); hydrogen In water at 80℃; under 15001.5 Torr; for 4h; Catalytic behavior; Reagent/catalyst; Time; Autoclave; Green chemistry;	99.9%
With iron(II) triflate; phenanthridine; triiron dodecarbonyl; hydrogen In 1,4-dioxane at 65℃; under 37503.8 Torr; for 24h; Autoclave;	91%

sodium cyanide (773837-37-9) + 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) → pantolactone (79-50-5)

Conditions	Yield
With sulfuric acid for 3h; pH=9.5; Reflux;	98.9%
With sulfuric acid In water at 100℃; for 1h;	86.9%

(+-)-2,4-dihydroxy-3,3-dimethyl-butyric acid (470-29-1) → pantolactone (79-50-5)

Conditions	Yield
With sulfuric acid at 80 - 85℃; for 3h; Temperature;	98.3%

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + hydrogen cyanide (74-90-8) → pantolactone (79-50-5)

Conditions	Yield
Stage #1: 2,2-dimethyl-3-hydroxypropionaldehyde; hydrogen cyanide In water at 0 - 10℃; for 0.25h; Stage #2: With sulfuric acid for 1h; Reflux;	93.1%
Verseifung des Reaktionsprodukts mit Salzsaeure;

(R,S)-2,4-Dihydroxy-3,3-dimethylbutyronitrile (10232-92-5) → pantolactone (79-50-5)

Conditions	Yield
With sulfuric acid for 6h; Reagent/catalyst; Reflux;	92.5%
With ammonium hydroxide; sulfuric acid at 94 - 96℃; under 435.044 Torr; for 2.25h; pH=5.0; Pressure; Temperature; pH-value; Inert atmosphere;

pantolactone p-nitrobenzoate (134734-33-1) → pantolactone (79-50-5)

Conditions	Yield
With lithium hydroxide In methanol; water for 0.166667h; Ambient temperature;	90%

N-benzyl-2,4-dihydroxy-3,3-dimethylbutyramide (100618-94-8) → pantolactone (79-50-5) + 1-benzyl-3-hydroxy-4,4-dimethylpyrrolidin-2-one

Conditions	Yield
With toluene-4-sulfonic acid In diethylene glycol dimethyl ether for 5h; Heating;	A 14 % Spectr. B 69%

glyoxylic acid ethyl ester (924-44-7) + 2-methyl-propan-1-ol (78-83-1) → pantolactone (79-50-5)

Conditions	Yield
Stage #1: glyoxylic acid ethyl ester; 2-methyl-propan-1-ol With N-(2-hydroxyethyl)pyrrolidine-2-carboxamide In toluene; tert-butyl alcohol at 20℃; for 24h; Stage #2: With [RhCl2(p-cymene)]2; sodium formate In water; toluene; tert-butyl alcohol Reagent/catalyst; Temperature; Inert atmosphere;	62%

N-heptyl-2,4-dihydroxy-3,3-dimethylbutyramide (43180-77-4) → pantolactone (79-50-5) + 1-heptyl-3-hydroxy-4,4-dimethylpyrrolidin-2-one

Conditions	Yield
With toluene-4-sulfonic acid In diethylene glycol dimethyl ether for 15h; Heating;	A 41% B 15%

(R,S)-2,4-Dihydroxy-3,3-dimethylbutyramide (4417-86-1) → DL-4-amino-2-hydroxy-3,3-dimethylbutanoic acid lactam (70006-38-1) + pantolactone (79-50-5)

Conditions	Yield
With ammonia; toluene-4-sulfonic acid In methanol at 250℃; under 7220 - 11400 Torr; for 4h; Heating;	A 9 % Spectr. B 40%

formaldehyd (50-00-0) + sodium 3-methyl-2-oxobutyrate (3715-29-5) → ketopantolactone (13031-04-4) + pantolactone (79-50-5)

Conditions	Yield
With hydrogenchloride; potassium carbonate 1.) H2O, 38-40 deg C, (well controlled addition of formaldehyde); Yield given. Multistep reaction. Yields of byproduct given;

calcium (S)-pantothenate (137-08-6, 867-80-1, 6381-62-0, 6381-63-1, 15773-29-2, 64789-49-7, 122484-60-0, 131346-21-9) → pantolactone (79-50-5) + 3-amino propanoic acid (107-95-9)

Conditions	Yield
With water; sodium 1,2-naphthoquinone-4-sulfonate In ethanol Kinetics; Rate constant; Mechanism; various temperatures, times, concentrations, pH, ionic strengths, and dielectric constants;

isobutyraldehyde (78-84-2) + oxalic acid diethyl ester (95-92-1) → ketopantolactone (13031-04-4) + dihydro-4,4-dimethyl-5-(1-methylethyl)-2,3-furandione (96305-22-5) + pantolactone (79-50-5)

Conditions	Yield
With formaldehyd; sodium methylate 1.) methanol, 10 deg C, 20 min, 2.) methanol, 40 deg C, 20 min; Yield given. Multistep reaction. Yields of byproduct given;

(RS)-2-acetoxy-3,3-dimethyl-γ-butyrolactone (28227-35-2) → pantolactone (79-50-5)

Conditions	Yield
With potassium hydroxide In methanol Heating; Yield given;

formaldehyd (50-00-0) + potassium-salt of/the/ α-oxo-isovaleric acid → ketopantolactone (13031-04-4) + pantolactone (79-50-5)

Conditions	Yield
With potassium carbonate Erwaermen der mit wss. Salzsaeure angesaeuerten Reaktionsloesung;

(+-)-2,4-dihydroxy-3,3-dimethyl-butyrimidic acid-4-lactone → pantolactone (79-50-5)

Conditions	Yield
With water

ketopantolactone (13031-04-4) + ethylmagnesium bromide (925-90-6) → pantolactone (79-50-5) + 2,2-diethyl-3-hydroxy-4,4-dimethyltetrahydrofuran

Conditions	Yield
In tetrahydrofuran at 0℃; for 1h; Title compound not separated from byproducts;

2,4-dihydroxy-N-phenyl-3,3-dimethylbutyramide (565430-86-6) → rac-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone (70006-37-0) + pantolactone (79-50-5)

Conditions	Yield
With toluene-4-sulfonic acid In diethylene glycol dimethyl ether for 15h; Heating;	A 40 % Spectr. B 53 % Spectr.

(R)-Pantolacton (599-04-2) → pantolactone (79-50-5)

Conditions	Yield
With Lactobacillus paracasei DSM 20207 In water at 42℃; for 24h; pH=6; Product distribution; Further Variations:; Reagents;

N-benzyl-2,4-dihydroxy-3,3-dimethylbutyramide (100618-94-8) → pantolactone (79-50-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 14 percent Spectr. / p-TsOH*H2O / bis-(2-methoxy-ethyl) ether / 5 h / Heating 2.1: n-BuLi / tetrahydrofuran; hexane / 3 h / 0 °C 2.2: 59 percent / tetrahydrofuran; hexane / 12 h / 20 °C 3.1: 53 percent Spectr. / p-TsOH*H2O / bis-(2-methoxy-ethyl) ether / 15 h / Heating View Scheme

2,4-dihydroxy-N-phenyl-3,3-dimethylbutyramide (565430-86-6) → pantolactone (79-50-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 53 percent Spectr. / p-TsOH*H2O / bis-(2-methoxy-ethyl) ether / 15 h / Heating 2: 100 percent / methanol / 24 h / 20 °C 3: 14 percent Spectr. / p-TsOH*H2O / bis-(2-methoxy-ethyl) ether / 5 h / Heating View Scheme

(3R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl methanesulfonate (20374-32-7) → pantolactone (79-50-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 38 percent / 18-crown-6 / benzene / 48 h / Heating 2: 5percent KOH / methanol / Heating View Scheme

Chloro-methanesulfonic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester (182243-70-5) → pantolactone (79-50-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / 18-crown-6 / benzene / 3 h / Heating 2: 5percent KOH / methanol / Heating View Scheme

(R)-Pantolacton (599-04-2) + taurine-p-toluidide → pantolactone (79-50-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 98 percent / pyridine / 0.17 h / 0 - 20 °C 2: 94 percent / 18-crown-6 / benzene / 3 h / Heating 3: 5percent KOH / methanol / Heating View Scheme
Multi-step reaction with 3 steps 1: 88 percent / pyridine / 0.17 h / 0 - 20 °C 2: 38 percent / 18-crown-6 / benzene / 48 h / Heating 3: 5percent KOH / methanol / Heating View Scheme

1-Heptylamine (111-68-2) + pantolactone (79-50-5) → N-heptyl-2,4-dihydroxy-3,3-dimethylbutyramide (43180-77-4)

Conditions	Yield
In methanol at 20℃; for 20h;	100%
at 100 - 110℃;
at 100 - 110℃;

diethylamine (109-89-7) + pantolactone (79-50-5) → N,N-Diethyl-2,4-dihydroxy-3,3-dimethyl-butyramide

Conditions	Yield
In acetonitrile at 30℃; under 6750540 Torr; for 168h;	100%

methylamine (74-89-5) + pantolactone (79-50-5) → β,β-dimethyl-α,γ-dihydroxybutyric acid N-methylamide (79691-41-1)

Conditions	Yield
In methanol; water at 20℃; for 3h;	100%
In water Ring cleavage;

benzylamine (100-46-9) + pantolactone (79-50-5) → N-benzyl-2,4-dihydroxy-3,3-dimethylbutyramide (100618-94-8)

Conditions	Yield
In methanol at 20℃; for 24h;	100%
In methanol for 3h; Ambient temperature;	93%

pantolactone (79-50-5) → (R,S)-2,4-Dihydroxy-3,3-dimethylbutyramide (4417-86-1)

Conditions	Yield
With ammonia at -60 - 20℃; Ring cleavage;	100%
With ammonium hydroxide In methanol at 20℃; for 14h;	84%
Multi-step reaction with 3 steps 1: 100 percent / methanol / 24 h / 20 °C 2: 14 percent Spectr. / p-TsOH*H2O / bis-(2-methoxy-ethyl) ether / 5 h / Heating 3: 84 percent / aq. NH3 / methanol / 14 h / 20 °C View Scheme

2-Methoxyethoxymethyl chloride (3970-21-6) + pantolactone (79-50-5) → 4,4-dimethyl-2-methoxyethoxymethoxy-γ-butyrolactone (915097-01-7)

Conditions	Yield
With 15-crown-5; sodium hydride In tetrahydrofuran at 22℃; for 15h;	100%

pantolactone (79-50-5) → ketopantolactone (13031-04-4)

Conditions	Yield
With oxygen In 1,2-dichloro-benzene at 180℃; for 3h;	99.5%
With trichloroisocyanuric acid; tetrabutylammomium bromide; water; potassium carbonate; ruthenium trichloride In acetonitrile at 20 - 45℃; for 1 - 3h; Product distribution / selectivity;	97.7%
With ruthenium(III) chloride trihydrate; trichloroisocyanuric acid; tetrabutylammomium bromide; sodium acetate In water; acetonitrile at 25 - 45℃; Green chemistry; chemoselective reaction;	97.7%

pantolactone (79-50-5) → potassium pantoate

Conditions	Yield
With water; potassium hydroxide at 60℃; for 4h;	99.2%

triethylmethoxystannane (1067-21-6) + pantolactone (79-50-5) → DL-2-triethylstannoxy-3,3-dimethyl-γ-butyrolactone (56150-63-1)

Conditions	Yield
In neat (no solvent) byproducts: MeOH; mixt. of the hydroxy deriv. and triethylmethoxystannane heated (formed MeOH removed continuously during react.); distn.; elem. anal.;	99%

benzyl bromide (100-39-0) + pantolactone (79-50-5) → 3-(benzyloxy)-4,4-dimethyldihydrofuran-2(3H)-one (117895-47-3)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; silver(l) oxide In dichloromethane at 20℃; for 48h; Darkness;	98%

pantolactone (79-50-5) → DL-sodium pantoate (1902-01-8)

Conditions	Yield
With water; sodium hydroxide at 60℃; for 4h;	96.3%
With sodium hydroxide In ethanol for 2h; Yield given;

chloromethyl methyl ether (107-30-2) + pantolactone (79-50-5) → 3,3-dimethyl-2-methoxymethoxy-4-butanolide (90113-81-8)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 40℃; for 24h;	96%

1-amino-3-(dimethylamino)propane (109-55-7) + pantolactone (79-50-5) → N-[3-(dimethylamino)propyl]-2,4-dihydroxy-3,3-dimethylbutyramide

Conditions	Yield
In 1,4-dioxane for 5h; Heating;	96%

1-hydroxygermatrane monohydrate (101151-96-6) + pantolactone (79-50-5) → DL-2-germatranoxy-3,3-dimethyl-γ-butyrolactone (133517-05-2)

Conditions	Yield
In m-xylene=m-xylol byproducts: H2O; mixt. of the germatrane with the hydroxy compd. in m-xylene refluxed with azeotropic distn. of H2O; residue filtered off, washed with n-pentane, recrystn. from CH3CN; elem. anal.;	96%

(1R,2R,3S,4S)-3-Amino-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-ol (29900-93-4) + pantolactone (79-50-5) → 2,4-dihydroxy-N-<(1R)-2-endo-hydroxy-3-endo-bornyl>-3,3-dimethylbutyramide

Conditions	Yield
In toluene at 110℃; for 1.5h;	95.7%

ethylamine (75-04-7) + pantolactone (79-50-5) → N-ethyl-2,4-dihydroxy-3,3-dimethylbutyramide (4417-90-7)

Conditions	Yield
In methanol for 3h; Ambient temperature;	95%
at 100℃;

aniline (62-53-3) + pantolactone (79-50-5) → rac-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone (70006-37-0)

Conditions	Yield
With toluene-4-sulfonic acid In methanol at 250℃; under 7220 - 11400 Torr; for 4h; Heating;	93%
	82%

methanesulfonyl chloride (124-63-0) + pantolactone (79-50-5) → 4,4-dimethyl-2-oxotetrahydro-3-furyl methane sulfonate (20664-78-2)

Conditions	Yield
With triethylamine In dichloromethane at -5℃;	92%

2,3-dihydro-2H-furan (1191-99-7) + pantolactone (79-50-5) → 3,3-dimethyl-2-(2-tetrahydrofuryloxy)-4-butanolide (371198-80-0)

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 0℃;	91%

cyclohexylamine (108-91-8) + pantolactone (79-50-5) → N-cyclohexyl-2,4-dihydroxy-3,3-dimethylbutyramide (16424-76-3)

Conditions	Yield
In methanol for 3h; Ambient temperature;	90%

N-butylamine (109-73-9) + pantolactone (79-50-5) → N-butyl-2,4-dihydroxy-3,3-dimethylbutyramide (43180-76-3)

Conditions	Yield
In methanol for 3h; Ambient temperature;	89%
at 100 - 110℃;
at 100 - 110℃;

propionic acid anhydride (123-62-6) + pantolactone (79-50-5) → (+/-)-pantolactone propionate

Conditions	Yield
With 4-pyrrolidin-1-ylpyridine; triethylamine In dichloromethane for 10h; Ambient temperature;	89%

Upstream product

• 28227-35-2 (RS)-2-acetoxy-3,3-dimethyl-γ-butyrolactone 
• 1902-01-8 DL-sodium pantoate 
• 75-36-5 acetyl chloride 
• 924-44-7 glyoxylic acid ethyl ester 
• 78-84-2 isobutyraldehyde 
• 597-31-9 2,2-dimethyl-3-hydroxypropionaldehyde 
• 74-90-8 hydrogen cyanide 
• 143-33-9 sodium cyanide 
• 151-50-8 potassium cyanide 
• 50-00-0 formaldehyd 
• 134734-33-1 pantolactone p-nitrobenzoate 
• 137-08-6 calcium (S)-pantothenate 
• 4417-86-1 (R,S)-2,4-Dihydroxy-3,3-dimethylbutyramide 
• 100618-94-8 N-benzyl-2,4-dihydroxy-3,3-dimethylbutyramide 

Downstream Products

• 134734-33-1 O-(4-nitro-benzoyl)-L-pantolactone 
• 101776-81-2 N-phenethyl-L-pantamide 
• 20664-72-6 O-(toluene-4-sulfonyl)-L-pantolactone 
• 326908-18-3 phthalic acid mono-(4,4-dimethyl-2-oxo-tetrahydro-[3]furyl ester) 
• 85508-39-0 L-pantothenic acid-((1R)-menthyl ester) 
• 111613-07-1 optically inactive pantothenic acid menthyl ester 
• 55685-38-6 3-benzoyloxy-4,4-dimethyl-dihydro-furan-2-one 
• 134734-33-1 pantolactone p-nitrobenzoate 
• 101776-81-2 N-phenethyl-DL-pantamide 
• 114554-83-5 1,1-bis-(4-dimethylamino-phenyl)-3,3-dimethyl-butane-1,2,4-triol 
• 114063-85-3 dicyclohexyl-amine; DL pantothenate 
• 409324-55-6 3-diphenoxyphosphoryloxy-4,4-dimethyl-dihydro-furan-2-one 
• 13031-04-4 ketopantolactone 
• 117895-47-3 3-(benzyloxy)-4,4-dimethyldihydrofuran-2(3H)-one 

Relevant articles and documents

Adsorption and stability of chiral modifiers based on 1-(1-naphthyl)-ethylamine for Pt catalysed heterogeneous asymmetric hydrogenations

Synthetic chiral modifiers suitable for modular build-up are highly desirable for tuning the efficiency and extending the versatility of asymmetric hydrogenations on chirally-modified metal catalysts. Adsorptive anchoring and structural stability of the simple chiral modifier (R)-1-(1-naphthyl)-ethylamine [(R)-NEA] and the upgraded, secondary amine chiral modifier (R,S)-pantoylnaphthylethylamine [(R,S)-PNEA] have been investigated under catalytic hydrogenation conditions. Using attenuated total reflection-infrared (ATR-IR) spectroscopy the adsorption modes of (R)-NEA and (R,S)-PNEA at the solid-liquid interface of a technical 5 wt% Pt/Al2O3 catalyst were investigated. In addition to the naphthalene group, (R,S)-PNEA is also anchored to Pt through its pantoyl moiety providing both enhanced anchoring and also a better defined chiral surface site for the asymmetric hydrogenation of ketopantolactone (KPL). Factors influencing the stability of NEA-based chiral modifiers are discussed. The recently discovered chiral fragmentation product of (R,S)-PNEA, (S)-amino-4,4-dimethyl-dihydrofuran-2-one [(S)-AF] is shown to play no role in conferring enantioselectivity in the asymmetric hydrogenation of KPL.

Preparation method of DL-pantoic acid lactone

The invention discloses a preparation method of DL-pantoic acid lactone, which comprises the following steps: reacting formaldehyde with isobutyraldehyde in the presence of a basic catalyst, slowly dropwise adding the reaction solution into sodium cyanide, adding an acid solution after the reaction is finished, and carrying out esterification reaction to obtain the DLpantoic acid lactone. The reaction is carried out in a water system, high-temperature and high-pressure reaction conditions are not needed, the process safety performance is high, the energy-saving and consumption-reducing effectsare obvious, and a high-content target product is obtained at a high yield, so that the production cost is reduced, and the method is a safe and simple DL-pantoic acid lactone production method.

Preparation method of hydroxyaldehyde and method for resolving optical isomer by using electrodialysis technology

The present invention provides a process for preparing hydroxyaldehydes using an immobilized catalyst, wherein the immobilized catalyst comprises a solid support and a tertiary amine-based functionalgroup. The invention also provides a method for preparing a polyhydroxy alcohol compound and a polyhydroxy acid compound. The invention further provides a method for splitting the optical isomer fromthe raceme through electrodialysis.