557-25-5

Basic information

• Product Name: 1-MONOBUTYRIN
• Synonyms: alpha-Monobutyrin;Butanoic acid, 2,3-dihydroxypropyl ester;butanoicacid,2,3-dihydroxypropylester;butanoicacid2,3-dihydroxypropylester;butyricacid2,3-dihydroxy-propylester;Butyrin, 1-mono-;Glycerol-alpha-mono-n-butyrate;Mono-n-butyrin
• CAS NO: 557-25-5
• Molecular Formula: C₇H₁₄O₄
• Molecular Weight: 162.18
• EINECS: 209-165-5
• Mol File: 557-25-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 153 °C (7 mmHg)
• Flash Point: 111.3°C
• Appearance: /
• Density: 1.09
• Vapor Pressure: 0.000453mmHg at 25°C
• Refractive Index: 1.445-1.453
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Sparingly)
• PKA: 13.16±0.20(Predicted)
• CAS DataBase Reference: 1-MONOBUTYRIN(CAS DataBase Reference)
• NIST Chemistry Reference: 1-MONOBUTYRIN(557-25-5)
• EPA Substance Registry System: 1-MONOBUTYRIN(557-25-5)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 557-25-5(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light yellow liquid

Uses

Glycerol 1-Monobutyrate functions as a key regulatory molecule in angiogenic process.

Definition

ChEBI: A 1-monoglyceride resulting from the formal esterification of butyric acid with one of the primary hydroxy groups of glycerol. The R enantiomer is bioactive.

InChI:InChI=1/C7H14O4/c1-2-3-7(10)11-5-6(9)4-8/h6,8-9H,2-5H2,1H3/t6-/m1/s1

Synthetic route

4-hydroxymethyl-1,3-dioxolan-2-one (931-40-8) + butyric acid (107-92-6) → 1-monobutyrin (557-25-5)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide at 140 - 142℃; for 24h; Reflux;	82%

sodium butyrate (156-54-7) + 3-monochloro-1,2-propanediol (96-24-2) → 1-monobutyrin (557-25-5)

glycerol (56-81-5) + butyric acid (107-92-6) → 1-monobutyrin (557-25-5)

Conditions	Yield
With tetrachloromethane; phosphoric acid

2-monobutyroylglycerol (70916-53-9) → 1-monobutyrin (557-25-5)

Conditions	Yield
In hexane at 30℃; for 168h; Rate constant; Equilibrium constant; Product distribution; var. reaction times; other β-monoglycerides;

tributyrin (60-01-5) → 1-monobutyrin (557-25-5) + β-dibutyrin (30403-46-4, 96739-06-9, 101469-20-9, 24814-35-5) + 1,3-dibutanoyloxy-2-propanol (17364-00-0)

Conditions	Yield
With lamb pregastric lipase at 35℃; for 0.35h; emulsifier, pH 7.o1; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With lamb pregastric lipase at 35℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

butyric acid (107-92-6) + d glycide → 1-monobutyrin (557-25-5)

Conditions	Yield
at 37℃; levorotatory form;

butyric acid (107-92-6) + l glycide → 1-monobutyrin (557-25-5)

Conditions	Yield
at 37℃; dextrorotatory form;

tributyrin (60-01-5) → 1-monobutyrin (557-25-5) + glycerol (56-81-5) + α.α'-dibutyryne

Conditions	Yield
enzymatische Hydrolyse durch Pankreaslipase; die Produkten entstehen nacheinander in drei Stufen mit verschiedener Geschwindigkeit;

butanoic acid anhydride (106-31-0) + glycerol (56-81-5) → 1-monobutyrin (557-25-5)

Conditions	Yield
With Candida antarctica In 1,4-dioxane at 15℃; for 2h;	43 % Chromat.

(2,2-dimethyl-1,3-dioxolane-4-yl)methyl n-butanoate (92418-59-2) → 1-monobutyrin (557-25-5)

Conditions	Yield
In methanol; ethyl acetate

methanol (67-56-1) + tributyrin (60-01-5) → 1-monobutyrin (557-25-5) + β-dibutyrin (30403-46-4, 96739-06-9, 101469-20-9, 24814-35-5) + butanoic acid methyl ester (623-42-7) + glycerol (56-81-5)

Conditions	Yield
magnesium-aluminum hydrotalcite at 59.84℃; Kinetics; Further Variations:; Catalysts;

glycerol (56-81-5) + butyric acid (107-92-6) → 1-monobutyrin (557-25-5) + 1,3-dibutanoyloxy-2-propanol (17364-00-0)

Conditions	Yield
With Ag(1+)*2H(1+)*PW12O40(3-)=AgH2PW12O40 at 120℃; for 0.25h; Autoclave; Green chemistry;

oxiranyl-methanol (556-52-5) + butyric acid (107-92-6) → 1-monobutyrin (557-25-5)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide at 120℃;

glycerol (56-81-5) + butyric acid (107-92-6) → 1-monobutyrin (557-25-5) + β-dibutyrin (30403-46-4, 96739-06-9, 101469-20-9, 24814-35-5) + 2-monobutyroylglycerol (70916-53-9) + 1,3-dibutanoyloxy-2-propanol (17364-00-0)

Conditions	Yield
With sulphonated hydrothermal carbon at 115℃; for 1h; Catalytic behavior; chemoselective reaction;

glycerol (56-81-5) + butyric acid (107-92-6) → tributyrin (60-01-5) + 1-monobutyrin (557-25-5) + β-dibutyrin (30403-46-4, 96739-06-9, 101469-20-9, 24814-35-5) + 2-monobutyroylglycerol (70916-53-9) + 1,3-dibutanoyloxy-2-propanol (17364-00-0)

Conditions	Yield
at 115℃; for 24h;

1-monobutyrin (557-25-5) + Methacryloyl chloride (920-46-7) → 3-(butyryloxy)propan-1,2-diyl bis(2-methylacrylate)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 3.5h; Inert atmosphere;	94%

1-monobutyrin (557-25-5) + acryloyl chloride (814-68-6) → 3-(butyryloxy)propan-1,2-diyl diacrylate

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 3.5h; Inert atmosphere;	91%

tetraethoxy orthosilicate (78-10-4) + 1-monobutyrin (557-25-5) → silicic acid tetrakis-(3-butyryloxy-2-hydroxy-propyl ester) (18759-74-5)

Conditions	Yield
at 140℃;

1-monobutyrin (557-25-5) → 2-n-butyryloxyacetaldehyde (136831-95-3)

Conditions	Yield
With periodic acid

1-monobutyrin (557-25-5) → 2-monobutyroylglycerol (70916-53-9)

Conditions	Yield
In hexane at 30℃; for 168h; Equilibrium constant;

1-monobutyrin (557-25-5) + periodic acid → glycolaldehyde-butyrate

tetraethoxy orthosilicate (78-10-4) + 1-monobutyrin (557-25-5) → Si{OCH(CH2OH)CH2OCOCH2CH2CH3}4

Conditions	Yield
at 150°C;;

Upstream product

• 156-54-7 sodium butyrate 
• 96-24-2 3-monochloro-1,2-propanediol 
• 56-81-5 glycerol 
• 107-92-6 butyric acid 
• 70916-53-9 2-monobutyroylglycerol 
• 60-01-5 tributyrin 
• 106-31-0 butanoic acid anhydride 
• 92418-59-2 (2,2-dimethyl-1,3-dioxolane-4-yl)methyl n-butanoate 
• 67-56-1 methanol 
• 931-40-8 4-hydroxymethyl-1,3-dioxolan-2-one 
• 556-52-5 oxiranyl-methanol 

Relevant articles and documents

Biobased catalyst in biorefinery processes: Sulphonated hydrothermal carbon for glycerol esterification

Sulphonated hydrothermal carbon (SHTC), obtained from d-glucose by mild hydrothermal carbonisation and subsequent sulphonation with sulphuric acid, is able to catalyse the esterification of glycerol with different carboxylic acids, namely, acetic, butyric and caprylic acids. Product selectivity can be tuned by simply controlling the reaction conditions. On the one hand, SHTC provides one of the best selectivity towards monoacetins described up to now without the need for an excess of glycerol. On the other hand, excellent selectivity towards triacylglycerides (TAG) can be obtained, beyond those described with other solid catalysts, including well-known sulphonic resins. Recovery of the catalyst showed partial deactivation of the solid. The formation of sulphonate esters on the surface, confirmed by solid state NMR, was the cause of this behaviour. Acid treatment of the used catalyst, with subsequent hydrolysis of the surface sulphonate esters, allows SHTC to recover its activity. The higher selectivity towards mono- and triesters and its renewable origin makes SHTC an attractive catalyst in biorefinery processes.

Design of a highly active silver-exchanged phosphotungstic acid catalyst for glycerol esterification with acetic acid

A series of highly active, selective, and stable silver-exchanged phosphotungstic acid (AgPW) catalysts were prepared, characterized, and evaluated for bio-derived glycerol esterification with acetic acid to produce valuable biofuel additives. The structures, morphologies, acidities, and water tolerance of these samples were determined by FTIR, Raman, XRD, SEM-EDX, FT-IR of pyridine adsorption, and H2O-TPD. Several typical acidic catalysts were also performed for comparison. Among them, partially silver-exchanged phosphotungstic acid (Ag1PW) presented exceptionally high activity, with 96.8% conversion within just 15 min of reaction time and remarkable stability, due to the unique Keggin structure, high acidity as well as outstanding water-tolerance property. A plausible reaction mechanism was also proposed. In addition, this Ag1PW catalyst exhibited universal significance for esterification, holding great potential for a wide range of other acid-catalyzed reactions.

Lipase-mediated desymmetrization of glycerol with aromatic and aliphatic anhydrides

Chirazyme L-2 (Candida antarctica) catalyzed esterification of glycerol with aromatic and aliphatic anhydrides in 1,4-dioxane is described. All the aromatic monoacylglycerols (MAGs) were produced as (R)-enantiomers, while aliphatic MAGs were obtained either as racemic mixtures or the (S)-enantiomers. The influence of substituted aromatic rings, chain length, and presence of a conjugated double bond in the acyl donor moiety on the enantiotopic selectivity as well as the efficiency of the enzyme was studied.