473-81-4

Basic information

• Product Name: glyceric acid
• Synonyms: glyceric acid;Propanoic acid, 2,3-dihydroxy-;C00258;DL-Glyceric Acid (20% in Water, ca. 2Mol/L);(20% in Water, ca. 2Mol/L);DL-Glyceric Acid 2,3-Dihydroxypropanoic acid[20% in water w/w];β-Hydroxylactic acid
• CAS NO: 473-81-4
• Molecular Formula: C₃H₆O₄
• Molecular Weight: 106.07734
• EINECS: 207-472-9
• Mol File: 473-81-4.mol
• Article Data: 206

Chemical Properties

• Melting Point: <25 °C
• Boiling Point: 412 °C at 760 mmHg
• Flash Point: 217.1 °C
• Appearance: /
• Density: 1.0304 (rough estimate)
• Vapor Pressure: 1.65E-08mmHg at 25°C
• Refractive Index: 1.5150 (estimate)
• Storage Temp.: 2-8°C
• PKA: 3.52(at 25℃)
• CAS DataBase Reference: glyceric acid(CAS DataBase Reference)
• NIST Chemistry Reference: glyceric acid(473-81-4)
• EPA Substance Registry System: glyceric acid(473-81-4)

Safety Data

• Hazardous Substances Data: 473-81-4(Hazardous Substances Data)

Usage

Description

Glyceric acid is a natural three - carbon sugar acid . Salts and esters of glyceric acid are known as glycerates.

Biotechnological Applications

Several phosphate derivatives of glyceric acid, including 2- phospho glyceric acid, 3-phosphoglyceric acid, 2,3-bi sphospho glyceric acid, and 1,3-bi sphospho glyceric acid, are important biochemical intermediates in Glycolysis.

InChI:InChI=1/C3H6O4/c4-1-2(5)3(6)7/h2,4-5H,1H2,(H,6,7)/t2-/m1/s1

Synthetic route

Glyceraldehyde (56-82-6) → glyceric acid (473-81-4)

Conditions	Yield
With 1 wt% Au/TiO2; oxygen In water at 75℃; under 39547.2 Torr; for 3022h; Time; Flow reactor;	100%
With sodium chlorite; dimethyl sulfoxide In aq. phosphate buffer at 0 - 20℃; pH=4;	93%
With iodine; sodium carbonate

glycerol (56-81-5) → glyceric acid (473-81-4)

Conditions	Yield
Stage #1: glycerol With Rh(OTf)(trop2NH)(PPh3); water; cyclohexanone; sodium hydroxide at 20℃; for 8h; Inert atmosphere; Stage #2: With hydrogenchloride In water Inert atmosphere; chemoselective reaction;	98%
With oxygen In water at 60℃; under 7500.75 Torr; Reagent/catalyst;	75%
With water; oxygen In water at 24.84℃; under 760.051 Torr; for 6h; Catalytic behavior; Schlenk technique;	42%

oxiranyl-methanol (556-52-5) → glyceric acid (473-81-4)

Conditions	Yield
Stage #1: oxiranyl-methanol With Rh(OTf)(trop2NH)(PPh3); water; cyclohexanone; sodium hydroxide at 20℃; for 8h; Inert atmosphere; Stage #2: With hydrogenchloride In water Inert atmosphere;	95%

2-Acetylamino-2,3-dibromo-propionic acid → acetamide (60-35-5) + glyceric acid (473-81-4)

Conditions	Yield
With sodium hydroxide; sodium tetrahydroborate In water for 4h; Product distribution; pH=10.8-11.0;	A n/a B 90%

glycerol (56-81-5) → glycolic Acid (79-14-1) + glyceric acid (473-81-4) + dihydroxyacetone (96-26-4)

Conditions	Yield
With oxygen In water at 60℃; Catalytic behavior; Reagent/catalyst; Autoclave; chemoselective reaction;	A 8.9% B 89.9% C 6.8%
With oxygen In water at 80℃; under 7500.75 Torr; for 2h; pH=6.7; Reagent/catalyst; Autoclave;
With oxygen In water at 60℃; under 3750.38 Torr; for 24h; Catalytic behavior; Kinetics; Reagent/catalyst; Time; High pressure;	A 7.8 %Chromat. B 55.4 %Chromat. C 7.7 %Chromat.

glycerol (56-81-5) → formaldehyd (50-00-0) + tartronic acid + glyceric acid (473-81-4) + dihydroxyacetone (96-26-4)

Conditions	Yield
With oxygen In water at 60℃; Catalytic behavior; Reagent/catalyst; Autoclave; chemoselective reaction;	A n/a B n/a C 84.9% D 6.5%

glycerol (56-81-5) → glyceric acid (473-81-4) + dihydroxyacetone (96-26-4) + Glyceraldehyde (56-82-6)

Conditions	Yield
With oxygen In water at 60℃; Catalytic behavior; Reagent/catalyst; Autoclave; chemoselective reaction;	A 84.2% B 9.5% C 6.3%
With oxygen In water at 60℃; under 760.051 Torr; for 4h; Catalytic behavior;
With Pt-MCM-41 catalyst; oxygen In water at 69.84℃; under 760.051 Torr; pH=Ca. 7; Kinetics; Catalytic behavior; Reagent/catalyst; Temperature;

glycerol (56-81-5) → glyceric acid (473-81-4) + Glyceraldehyde (56-82-6)

Conditions	Yield
With perchloric acid In ethanol at 20℃; pH=1; Concentration; Reagent/catalyst; Electrochemical reaction;	A 9% B 70.6%
With Pseudomonas putida HK-5 pyrroloquinoline quinone-dependent alcohol dehydrogenase; 4,4'-azobis(1-methylpyridinium) bis(methyl sulfate); NADH In aq. buffer for 6h; pH=7.1; Catalytic behavior; Time; Electrolysis; Enzymatic reaction;	A 53% B 15%
With silica-supported platinum; oxygen In water at 89.84℃; for 24h;

glycerol (56-81-5) → tartronic acid (80-69-3) + glyceric acid (473-81-4) + oxalic acid (144-62-7)

Conditions	Yield
With water; oxygen In water at 24.84℃; under 760.051 Torr; for 6h; Catalytic behavior; Schlenk technique;	A 10% B 54% C 5%
With oxygen; sodium hydroxide In water at 59.84℃; under 760.051 Torr; for 7h; Product distribution / selectivity; Closed type batch reactor;	A n/a B 70 %Chromat. C n/a
With oxygen; sodium hydroxide In water at 60℃; under 2250.23 Torr; for 24h;

glycerol (56-81-5) → LACTIC ACID (849585-22-4) + glyceric acid (473-81-4)

Conditions	Yield
With oxygen; sodium hydroxide In water at 70℃; pH=3.56; Temperature; pH-value; Flow reactor;	A 38% B 47.3%
With oxygen; sodium hydroxide In water at 89.84℃; under 760.051 Torr;
With sodium hydroxide at 90℃; under 760.051 Torr; Reagent/catalyst;
With oxygen; sodium hydroxide In water at 50℃; under 2250.23 Torr; Catalytic behavior;
With oxygen; sodium hydroxide at 110℃; under 2250.23 Torr; for 0.5h; Reagent/catalyst;

glycerol (56-81-5) → LACTIC ACID (849585-22-4) + tartronic acid (80-69-3) + glyceric acid (473-81-4)

Conditions	Yield
With oxygen; sodium hydroxide In water at 85℃; pH=3.56; Temperature; pH-value; Flow reactor;	A 46.5% B 5.5% C 38.1%
With oxygen; sodium hydroxide In water at 50℃; under 2250.23 Torr; for 4h; Catalytic behavior;
With lithium hydroxide monohydrate at 90℃; under 760.051 Torr; for 6h; Catalytic behavior; Inert atmosphere;

glycerol (56-81-5) → LACTIC ACID (849585-22-4) + glyceric acid (473-81-4) + dihydroxyacetone (96-26-4) + acetic acid (64-19-7) + Glyceraldehyde (56-82-6)

Conditions	Yield
With oxygen In water at 60℃; under 3750.38 Torr; for 5h; Catalytic behavior; Autoclave;	A 45% B n/a C n/a D n/a E n/a

glycerol (56-81-5) → glycolic Acid (79-14-1) + tartronic acid (80-69-3) + glyceric acid (473-81-4) + oxalic acid (144-62-7)

Conditions	Yield
With water; oxygen In water at 24.84℃; under 760.051 Torr; for 6h; Catalytic behavior; Reagent/catalyst; Concentration; Schlenk technique;	A 11% B 13% C 42% D 12%
With potassium carbonate In water at 80℃; for 24h;
With water; oxygen; sodium hydroxide at 50℃; under 2280.15 Torr; Reagent/catalyst;

allyl alcohol (107-18-6) → glyceric acid (473-81-4) + acrylic acid (79-10-7) + 3-hydroxypropionic acid (503-66-2)

Conditions	Yield
With oxygen; sodium hydroxide In water at 50℃; Reagent/catalyst; Sonication;	A 6.9% B 30.1% C 7.2%

D-lyxose (87-72-9, 608-45-7, 608-46-8, 608-47-9, 2460-44-8, 6748-95-4, 6763-34-4, 7261-26-9, 7283-06-9, 7283-07-0, 7296-55-1, 7296-56-2, 7296-58-4, 7296-59-5, 7296-60-8, 7296-61-9, 7296-62-0, 7322-30-7, 10257-31-5, 10257-32-6, 10257-33-7, 10257-34-8, 10257-35-9, 19982-83-3, 20242-88-0, 28697-53-2, 36562-42-2, 41546-41-2, 89299-64-9, 107655-34-5, 115794-06-4, 115794-07-5, 130550-15-1, 130606-21-2) → formic acid (64-18-6) + glycolic Acid (79-14-1) + glyceric acid (473-81-4) + carbon dioxide (124-38-9) + 2,3,4-Trihydroxybutanoic acid (10191-35-2)

Conditions	Yield
With copper(II) sulfate at 100℃; Product distribution; Rate constant; Thermodynamic data; study of the oxidation reaction of D-lyxose by cupric ion, kinetic mesurements, ΔS(excit.),;	A 14% B 30% C 22% D 15% E 12%

D-glucose (50-99-7) → glycolic Acid (79-14-1) + glyceric acid (473-81-4)

Conditions	Yield
With oxygen In water at 160℃; under 13680.9 Torr; for 20h; Temperature; Pressure; Reagent/catalyst; Green chemistry;	A 29.3% B 17.8%
With oxygen In water at 160℃; under 13680.9 Torr; for 20h;

allyl alcohol (107-18-6) → glyceric acid (473-81-4) + 3-hydroxypropionic acid (503-66-2)

Conditions	Yield
With cerium(IV) oxide Reagent/catalyst;	A 19% B 23.2%
With nano gold salt supported on cerium oxide	A 10.7% B 9.4%

glycerol (56-81-5) → glycolic Acid (79-14-1) + glyceric acid (473-81-4) + Glyceraldehyde (56-82-6)

Conditions	Yield
With perchloric acid In ethanol at 20℃; pH=1; Reagent/catalyst; Electrochemical reaction;	A 7% B 7.6% C 20.3%

Glyceraldehyde (56-82-6) → formic acid (64-18-6) + glyceric acid (473-81-4)

Conditions	Yield
With carbon dioxide; hydrogen; oxygen In water at 30℃; under 8274.59 Torr; for 6h; Catalytic behavior; Reagent/catalyst; Time; Autoclave;	A 14% B 10%

cellulose → LACTIC ACID (849585-22-4) + propylene glycol (57-55-6) + glyceric acid (473-81-4) + D-sorbitol (50-70-4) + ethylene glycol (107-21-1)

Conditions	Yield
With hydrogen In water at 240℃; under 30003 Torr; for 1h;	A 12.6% B 11.6% C 10.2% D 10.1% E 9.1%

D-Fructose (57-48-7) → glyceric acid (473-81-4)

Conditions	Yield
With copper(II) hydroxide; sodium hydroxide

D-Mannose (3458-28-4) → glyceric acid (473-81-4)

Conditions	Yield
With copper(II) hydroxide; sodium hydroxide

2,3-diaminopropanoic acid (515-94-6) → glyceric acid (473-81-4)

Conditions	Yield
im Tierkoerper;
With cis-nitrous acid

serin (302-84-1) → glyceric acid (473-81-4)

Conditions	Yield
With cis-nitrous acid
With hydrogenchloride; sodium nitrite In water at 0 - 20℃; for 17.0833h; Schlenk technique; Inert atmosphere;

(RS)-isoserine (632-12-2) → glyceric acid (473-81-4)

Conditions	Yield
With cis-nitrous acid at 40 - 50℃;

2,3-dibromopropionic acid (600-05-5) → glyceric acid (473-81-4)

Conditions	Yield
With water; silver(l) oxide

L-arabinose (5328-37-0) → glyceric acid (473-81-4)

Conditions	Yield
With copper(II) hydroxide; sodium hydroxide
With air in alkalischer Loesungen;
With dihydrogen peroxide in alkalischer Loesungen;

D-glucose (50-99-7) → glyceric acid (473-81-4)

Conditions	Yield
With copper(II) hydroxide; sodium hydroxide
With air in alkalischer Loesungen;
With dihydrogen peroxide in alkalischer Loesungen;

D-Galactose (59-23-4) → glyceric acid (473-81-4)

Conditions	Yield
With Fehling's solution
With air in alkalischer Loesungen;
With dihydrogen peroxide in alkalischer Loesungen;

(+/-)-calcium glycerate dihydrate (67525-74-0) → glyceric acid (473-81-4)

Conditions	Yield
Gaerung durch den Bacillus aethaceticus;

glyceric acid (473-81-4) → 3-iodopropanoic acid (141-76-4)

Conditions	Yield
With hydrogen iodide; hydrogen; palladium dichloride at 100℃; under 20686.5 Torr; for 10h; Reagent/catalyst; Temperature; Sealed tube;	99%
With hydrogen iodide; hydrogen; palladium dichloride In water at 100℃; under 20686.5 Torr; for 10h; Pressure; Reagent/catalyst; Temperature;	99%
With hydrogen iodide; hydrogen; palladium dichloride at 170℃; under 155149 Torr; for 25h; Temperature; Pressure; Sealed tube;	99.9%

methanol (67-56-1) + glyceric acid (473-81-4) → methyl glycerate (615-34-9)

Conditions	Yield
With toluene-4-sulfonic acid In water for 12h; Inert atmosphere; Reflux;	99%
With boron trifluoride methanol complex for 1h; Heating;	75.7%
at 180℃; methyl ester of/the/ d-glyceric acid;

glyceric acid (473-81-4) + mono(6-amino-6-deoxy)-per(2,3,6-O-methyl)-β-cyclodextrin (129867-48-7) → 6I-(2,3-dihydroxypropionamido)-6I-deoxy-2I,3I-di-O-methylhexakis(2II-VII,3II-VII,6II-VII-tri-O-methyl)cyclomaltoheptaose (1407657-67-3)

Conditions	Yield
Stage #1: glyceric acid With benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 1.5h; Inert atmosphere; Stage #2: mono(6-amino-6-deoxy)-per(2,3,6-O-methyl)-β-cyclodextrin With triethylamine In chloroform; N,N-dimethyl-formamide at 20℃; for 2.5h; Inert atmosphere;	91%

glyceric acid (473-81-4) → tartronic acid (80-69-3)

Conditions	Yield
With oxygen In water at 60℃; under 2250.23 Torr; for 9h; Mechanism; Autoclave;	75%

glyceric acid (473-81-4) + N1-(5-((2,6-dichloro-3,5-dimethoxybenzyl)oxy)pyrimidin-2-yl)-6-methylbenzene-1,2-diamine → N-(2-((5-((2,6-dichloro-3,5-dimethoxybenzyl)oxy)pyrimidin-2-yl)amino)-3-methylphenyl)-2,3-dihydroxypropanamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;	67%

glyceric acid (473-81-4) → formic acid (64-18-6) + glycolic Acid (79-14-1)

Conditions	Yield
With aluminium(III) triflate; dihydrogen peroxide In acetonitrile at 70℃; for 12h;	A 57.8% B 8.1%

glyceric acid (473-81-4) → 3-iodopropanoic acid (141-76-4) + 2,3-diiodopropionic acid

Conditions	Yield
With rhodium on carbon; hydrogen iodide; hydrogen; iodine In water at 99.84℃; under 20686.5 Torr; for 1h; Reagent/catalyst; Temperature; Autoclave;	A 52% B 14%

glyceric acid (473-81-4) + 3,3'-((2,2'-dichloro-[1,1'-biphenyl]-3,3'-diyl)bis(oxy))bis(propan-1-amine) + trifluoroacetic acid (76-05-1) → N,N'-(((2,2'-dichloro-[1,1'-biphenyl]-3,3'-diyl)bis(oxy))bis(propane-3,1-diyl))bis(2,3-dihydroxypropanamide) trifluoroacetate

Conditions	Yield
Stage #1: glyceric acid; 3,3'-((2,2'-dichloro-[1,1'-biphenyl]-3,3'-diyl)bis(oxy))bis(propan-1-amine) With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water; N,N-dimethyl-formamide at 20℃; for 18h; Stage #2: trifluoroacetic acid In water; acetonitrile	50%

glyceric acid (473-81-4) + benzyl bromide (100-39-0) → rac-benzyl 2,3-dihydroxypropanoate (73573-57-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 48h;	46%

ethanol (64-17-5) + glyceric acid (473-81-4) → ethyl 2,3-dihydroxypropionate (615-51-0)

Conditions	Yield
With hydrogenchloride Heating;	32%
at 180 - 190℃; ethyl ester of/the/ d-glyceric acid;
at 190℃; Man fraktionert das Produkt im Vakuum;
at 190℃;

glyceric acid (473-81-4) + C23H38MnN6O4 → C29H46MnN6O10

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; potassium hydroxide In water at 20℃; pH=6 - 7;	32%

glyceric acid (473-81-4) + 6-(3-fluoro-4-methoxybenzyl)-2,3,4,7-tetrahydro-1H-indolo[2,3-c][1,7]naphthyridine (1207632-14-1) → 1-[6-(3-fluoro-4-methoxybenzyl)-1,2,4,7-tetrahydro-3H-indolo[2,3-c][1,7]naphthyridin-3-yl]-2,3-dihydroxypropan-1-one (1207633-34-8)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane; water at 20℃; for 18h; Molecular sieve;	25%

Upstream product

• 7697-37-2 nitric acid 
• 56-81-5 glycerol 
• 57-48-7 D-Fructose 
• 7732-18-5 water 
• 807306-71-4 3,7-bis(dimethylamine)phenothiazonium 
• 55-63-0 glycerin trinitrate 
• 7647-01-0 hydrogenchloride 
• 177566-14-2 (R)-2-((S)-carboxy-methoxy-methoxy)-3-hydroxy-propionic acid 
• 28564-83-2 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one 
• 107-18-6 allyl alcohol 
• 453-17-8 D-Glyceraldehyde 
• 312-84-5 D-Serine 
• 473-81-4 glyceric acid 
• 50-99-7 D-glucose 

Downstream Products

• 473-81-4 D-glyceric acid 
• 473-81-4 (S)-glyceric acid 
• 64-18-6 formic acid 
• 513-86-0 3-hydroxy-2-butanon 
• 64-19-7 acetic acid 
• 75-07-0 acetaldehyde 
• 141-46-8 Glycolaldehyde 
• 77-92-9 citric acid 
• 3443-57-0 D-(+)-2-phosphoglyceric acid 
• 820-11-1 D-(-)-3-phosphoglyceric acid 
• 141-76-4 3-iodopropanoic acid 
• 6628-21-3 ethyl 2,3-dichloropropionate 
• 615-34-9 methyl glycerate 
• 56-45-1 L-serin 

Relevant articles and documents

Electro-oxidation of glycerol into formic acid by nickel-copper electrocatalysts

Herein, non-precious metallic nickel-copper electrocatalysts were synthesized for electro-oxidation of glycerol in alkaline electrolytes. Activated carbon felt (ACF) is used as a supporting material because of its good conductivity, chemical inertness, and porous structure which is conducive to the transport of the reactants/electrons. The structural features of the catalysts were characterized by scanning electron microscopy, X-ray diffraction and X-ray photoelectron spectroscopy. The electrochemical activity of the catalysts was revealed by cyclic voltammetry, linear sweeping voltammetry, and chronoamperometry. The electrochemical results show that the Cu1Ni1@ACF catalyst possesses the highest current density of 1.31 mA cm-2 at 1.895 V. High-performance liquid chromatography results show that the as-prepared catalysts have high selectivities for formic acid (FA). Especially, the Cu1Ni1@ACF catalyst yields a selectivity of 97.4% for FA, which has so far been the largest value reported in the literature. Additionally, the effects of applied potentials and reaction time on product selectivity were studied.

Assembly of platinum nanoparticles and single-atom bismuth for selective oxidation of glycerol

Selective oxidation of the secondary hydroxyl group of glycerol to dihydroxyacetone (DHA) is an extremely challenging yet important reaction. The main difficulty is that the three hydroxyl groups in glycerol are prone to randomly oxidize, resulting in an unsatisfactory DHA selectivity. We show here that an assembly of platinum nanoparticles (NPs, ～2 nm) and N-stabilized single-atom bismuth (Bi), namely Pt/Bi@NC, shows a record-high DHA selectivity of ～95.0% towards glycerol oxidation under optimized reaction conditions. Characterization and theoretical calculations confirm that single-atom Bi in the vicinity of Pt NPs provides a preferred site to chelate with the primary -OH of glycerol, and its secondary -OH is prone to bind to a surface Pt atom of a Pt NP with a shorter Pt-H bond length. This as-formed unique adsorption configuration of glycerol on the Pt-Bi dual site significantly facilitates the oxidation of the secondary -OH of glycerol, thus contributing to a record-high selectivity to DHA. This journal is

Transfer hydrogenation of CO2into formaldehyde from aqueous glycerol heterogeneously catalyzed by Ru bound to LDH

Aqueous glycerol was used in this study as a liquid-phase hydrogen source for the hydrogenation of CO2. It was found that hydrogen could be efficiently evolved from aqueous glycerol upon highly dispersed Ru on layered double hydroxide (LDH), inducing the transformation of CO2 into formaldehyde under base-free conditions at low temperature.