Butanedioic acid,2,3-dihydroxy-, (2R,3S)-rel- supplier

Name
MESOTARTARIC ACID
EINECS 205-696-1
CAS No. 147-73-9
Article Data77
CAS DataBase
Density 1.886 g/cm³
Solubility slightly soluble in water, ethanol, ethyl ether
Melting Point 165-166 ºC
Formula C₄H₆O₆
Boiling Point 399.3 °C at 760 mmHg
Molecular Weight 150.088
Flash Point 209.4 °C
Transport Information
Appearance white to off-white crystalline powder
Safety 26-36/37
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Butanedioicacid, 2,3-dihydroxy-, (R*,S*)-;Tartaric acid, meso- (8CI);(R,S)-Tartaricacid;Erythraric acid;Mesotartaric acid;i-Tartaric acid;meso-Tartaric acid;
PSA 115.06000
LogP -2.12260

Synthetic route

: 98-01-1
furfural

A: 108-31-6
maleic anhydride

B: 147-73-9
meso-tartaric acid

Conditions

Conditions	Yield
With vanadia at 370℃;

: 98-01-1
furfural

: 147-73-9
meso-tartaric acid

Conditions

Conditions	Yield
With sodium chlorate; osmium(VIII) oxide; water at 50℃;
With hydrogenchloride; sodium chlorate; osmium(VIII) oxide at 50℃;

: 108-31-6
maleic anhydride

: 147-73-9
meso-tartaric acid

Conditions

Conditions	Yield
With osmium(VIII) oxide; barium chlorate; water
With osmium(VIII) oxide; silver(I) chlorate; water

: 88-14-2
2-furanoic acid

: 147-73-9
meso-tartaric acid

Conditions

Conditions	Yield
With sodium chlorate; osmium(VIII) oxide; water at 50℃;
With hydrogenchloride; sodium chlorate; osmium(VIII) oxide at 50℃;

: 57-48-7
D-Fructose

: 147-73-9
meso-tartaric acid

Conditions

Conditions	Yield
With nitric acid

: 19700-96-0, 19700-97-1, 58208-04-1, 112571-38-7, 144829-86-7, 1069-23-4
hexa-1,5-diene-3,4-diol

: 147-73-9
meso-tartaric acid

Conditions

Conditions	Yield
With ozone; acetic acid Kochen des Diozonids und Erwaermen der mit Wasser verd.Loesung mit Brom auf 50grad,entsteht in analoger Reaktion aus Hydrocinnamoindiacetat;

: 1113-60-6
3-hydroxy-2-oxopropionic acid

: 151-50-8
potassium cyanide

A: 147-71-7
D-tartaric acid

B: 147-73-9
meso-tartaric acid

Conditions

Conditions	Yield
beim Kochen des Reaktionsprodukts mit verd.Schwefelsaeure;

...Expand

: 62842-54-0
DL-erythro-pentyne-(1)-triol-(3.4.5)

: 147-73-9
meso-tartaric acid

Conditions

Conditions	Yield
With nitric acid at 50 - 55℃;

: 527-52-6
D-digitxose

A: 33054-05-6, 34321-30-7, 34693-49-7, 82864-78-6
L-erythro-2.3-dihydroxy-glutaric acid

B: 147-73-9
meso-tartaric acid

Conditions

Conditions	Yield
With nitric acid at 90℃;

: 527-52-6
D-digitxose

: 147-73-9
meso-tartaric acid

Conditions

Conditions	Yield
With nitric acid

: 50-99-7
D-glucose

A: 147-73-9
meso-tartaric acid

B: 87-69-4
L-Tartaric acid

Conditions

Conditions	Yield
With sodium vanadate; nitric acid
With sodium vanadate; nitric acid
With sodium vanadate; nitric acid

: 23220-52-2
(2S,3R)-3-aminoaspartic acid

: 147-73-9
meso-tartaric acid

Conditions

Conditions	Yield
With nitric acid

: 87-69-4
L-Tartaric acid

: 147-73-9
meso-tartaric acid

Conditions

Conditions	Yield
With sodium hydroxide
With potassium hydroxide
With water at 165℃;

: 87-69-4
L-Tartaric acid

A: 147-73-9
meso-tartaric acid

: 133-37-9
DL-tartaric acid

Conditions

Conditions	Yield
With water
With hydrogenchloride
With hydrogenchloride im geschlossenen Rohr;
With sodium hydroxide; water

: 133-37-9
DL-tartaric acid

: 147-73-9
meso-tartaric acid

Conditions

Conditions	Yield
With water at 165℃;
With hydrogenchloride
With alkaline solution ueber den Verlauf dieser Reaktion;

: 74841-95-5
(-)(2S:3S)-3-chloro-2-hydroxy-succinic acid

A: 147-73-9
meso-tartaric acid

B: 87-69-4
L-Tartaric acid

Conditions

Conditions	Yield
With water

: 76-30-2
dihydroxytartaric acid

A: 147-73-9
meso-tartaric acid

: 133-37-9
DL-tartaric acid

Conditions

Conditions	Yield
With zinc

: 87-69-4
tartaric acid

: 147-73-9
meso-tartaric acid

Conditions

Conditions	Yield
With potassium hydroxide; water Darstellung; ueber mehrere Stufen;

: 87-69-4
tartaric acid

A: 147-73-9
meso-tartaric acid

: 133-37-9
DL-tartaric acid

Conditions

Conditions	Yield
With hydrogenchloride
With water
With alkaline solution

: 110-16-7
maleic acid

: 147-73-9
meso-tartaric acid

Conditions

Conditions	Yield
With osmium(VIII) oxide; potassium chlorate; water at 50℃;
With potassium permanganate
With sodium chlorate; osmium(VIII) oxide; water at 50℃;

: 110-16-7
maleic acid

A: 147-73-9
meso-tartaric acid

B: 144-62-7
oxalic acid

Conditions

Conditions	Yield
With osmium(VIII) oxide; dihydrogen peroxide; tert-butyl alcohol

: 56-81-5
glycerol

: 147-73-9
meso-tartaric acid

Conditions

Conditions	Yield
With nitric acid

: 17015-08-6
(2R,3R)-oxirane-2,3-dicarboxylic acid

A: 147-73-9
meso-tartaric acid

B: 87-69-4
L-Tartaric acid

Conditions

Conditions	Yield
With water
With potassium hydroxide

: 108-95-2
phenol

: 147-73-9
meso-tartaric acid

Conditions

Conditions	Yield
With permanganate(VII) ion at 0℃;

: 29781-80-4
octyl alpha-D-glucopyranoside

A: 80-69-3
tartronic acid

B: 147-73-9
meso-tartaric acid

C: 87-69-4
L-Tartaric acid

D: 526-95-4
gluconic acid

E: 87-73-0
D-glucaric acid

F: 144-62-7
oxalic acid

Conditions

Conditions	Yield
With oxygen; platinum on activated charcoal In water at 49.9℃; under 300.02 Torr; Product distribution; Mechanism; initial rate of consumption, pH effect;

...Expand

: 97-30-3
methyl-alpha-D-glucopyranoside

A: 80-69-3
tartronic acid

B: 473-81-4, 600-19-1, 6000-40-4, 28305-26-2
D-glyceric acid

C: 147-73-9
meso-tartaric acid

D: 87-69-4
L-Tartaric acid

E: 144-62-7
oxalic acid

Conditions

Conditions	Yield
With oxygen; platinum on activated charcoal In water at 49.9℃; under 300.02 Torr; Product distribution; Mechanism; initial rate of consumption, pH effect;

...Expand

: 6556-12-3, 489-91-8, 528-16-5, 552-12-5, 577-46-8, 643-33-4, 2240-07-5, 6294-16-2, 10133-02-5, 18402-78-3, 18968-14-4, 21179-08-8, 23018-83-9, 33599-45-0, 33599-46-1, 46171-67-9, 46171-69-1, 46172-26-3, 70021-34-0, 71031-08-8, 104195-06-4, 106499-29-0, 124817-72-7
D-glucuronic acid

A: 147-73-9
meso-tartaric acid

B: 728879-26-3
D-arabinuronic acid

C: 488-31-3, 608-54-8, 608-55-9, 6703-05-5, 10158-64-2, 20869-04-9, 33012-62-3
(2S,4S)-xylaric acid

D: 87-73-0
D-glucaric acid

Conditions

Conditions	Yield
With phosphate buffer; dihydrogen peroxide; iron(II) sulfate In water at 37℃; for 6h; pH=7.4; Product distribution; Further Variations:; Reagents; Oxidation;

...Expand

: 7732-18-5
water

: 7722-84-1
dihydrogen peroxide

: 75-65-0
tert-butyl alcohol

: 71-43-2
benzene

osmium(VIII)-oxide: osmium(VIII)-oxide

A: 147-73-9
meso-tartaric acid

B: 144-62-7
oxalic acid

C: 108-95-2
phenol

D allo-2,3,4,5-tetrahydroxy-adipic acid: allo-2,3,4,5-tetrahydroxy-adipic acid

...Expand

α.β-dibromo-β-trichloroacetyl-propionic acid: α.β-dibromo-β-trichloroacetyl-propionic acid

: 147-73-9
meso-tartaric acid

Conditions

Conditions	Yield
With calcium hydroxide

: 147-73-9
meso-tartaric acid

: 108-24-7
acetic anhydride

: 250137-64-5, 945416-40-0
(3R,4S)-2,5-dioxotetrahydrofuran-3,4-diyl diacetate

Conditions

Conditions	Yield
at 80℃; for 4h;	98.73%
With hydrogenchloride Acetylation; dehydration;	51%
With sulfuric acid at 120℃; for 1h; Inert atmosphere;	37%
With sulfuric acid for 4h;

: 147-73-9
meso-tartaric acid

: 1-ethyl-3-methylimidazolium hydroxide

: 1-ethyl-3-methylimidazolium meso-tartrate

Conditions

Conditions	Yield
In water at 20℃; for 2h; Darkness;	97%

: 147-73-9
meso-tartaric acid

: (E)-N-((1s,4s)-4-(dimethylamino)-1,4-diphenylcyclohexyl)-N-methylcinnamamide

: (E)-N-((1s,4s)-4-(dimethylamino)-1,4-diphenylcyclohexyl)-N-methylcinnamamide hemi-meso-tartrate

Conditions

Conditions	Yield
In isopropyl alcohol at 30℃; for 22h;	95.63%

: 147-73-9
meso-tartaric acid

: 1308671-66-0
5,5-difluoro-10-mesityl-1,3,7,9-tetramethyl-5H-4λ4,5λ4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine

: C48H52B2N4O6

Conditions

Conditions	Yield
With chloro-trimethyl-silane In acetonitrile at 120℃; for 4h; Microwave irradiation;	95%

: 147-73-9
meso-tartaric acid

: 870753-29-0
8-mesityl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene

: C40H36B2N4O6

Conditions

Conditions	Yield
With chloro-trimethyl-silane In acetonitrile at 120℃; for 8h; Microwave irradiation;	95%

: 508233-74-7
vortioxetine

: 147-73-9
meso-tartaric acid

: 1-[2-(2,4-dimethylphenylsulfanyl)-phenyl]piperazine meso-tartrate

Conditions

Conditions	Yield
In acetone at 20℃; for 0.5h;	93%
In acetone at 20℃; for 0.5h;	93%

: 67-56-1
methanol

: 147-73-9
meso-tartaric acid

: 77-76-9
2,2-dimethoxy-propane

: 6134-82-3
dimethyl meso-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In cyclohexane for 48h; Heating;	92%
toluene-4-sulfonic acid

...Expand

: 147-73-9
meso-tartaric acid

: 85100-77-2
1-n-butyl-3-methylimidazolim bromide

: 1-butyl-3-methylimidazolium meso-tartrate

Conditions

Conditions	Yield
Stage #1: meso-tartaric acid With silver (II) carbonate In water-d2 at 20℃; for 2h; Darkness; Stage #2: 1-n-butyl-3-methylimidazolim bromide In water-d2 at 20℃; Darkness;	92%

: 674-82-8
4-methyleneoxetan-2-one

: 147-73-9
meso-tartaric acid

: C12H14O10

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 55℃; for 4h; Reagent/catalyst; Solvent; Temperature;	91.2%

: 147-73-9
meso-tartaric acid

: 441785-25-7
Besifovir

: C4H6O6*C10H14N5O4P

Conditions

Conditions	Yield
In hexane; isopropyl alcohol at 45 - 50℃;	90.2%

: 147-73-9
meso-tartaric acid

: C24H33FN2O

: 2C24H33FN2O*C4H6O6

Conditions

Conditions	Yield
In ethanol at 45℃; for 0.666667h;	89.6%

: silver tartrate

: (+)-(.LAMDA.)-{Co(en)2(NO2)2}Br

: 147-73-9
meso-tartaric acid

: (+)589-(.LAMDA.,δ,δ)-cis-bis(ethylenediamine)dinitrocobalt(III) hydrogen D-tartrate monohydrate

Conditions

Conditions	Yield
In water stirring (+)-(.LAMDA.)-(Co(en)2(NO2)2)Br, Ag2tart, and H2tart in H2O at room temp. for 20 min; AgBr ppt. filtered, filtrate reduced to half vol., scratching surface of beaker, first crop of cryst. deposited, 2nd crop on further reducing the vol., recrystn. from hot (333°K) water, anal. by x-ray diffraction;	89%

...Expand

: 67-56-1
methanol

: 147-73-9
meso-tartaric acid

: 608-69-5, 13171-64-7, 117356-23-7, 608-68-4, 5057-96-5
dimethyl meso-tartrate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 20h; Reflux;	88%
With hydrogenchloride ice bath;	67.5%
With thionyl chloride at 0℃; for 4h; Reflux; Inert atmosphere;	32%
With Amberlyst-15

: 147-73-9
meso-tartaric acid

: 3,3’-di-n-octyl-1,1’-(1,4-phenylenedimethylene)diimidazolium dibromide

: 3,3'-di-n-octyl-1,1'(1,4-phenylenedimethylene)diimidazolium meso-tartrate

Conditions

Conditions	Yield
Stage #1: 3,3’-di-n-octyl-1,1’-(1,4-phenylenedimethylene)diimidazolium dibromide With Amberlite resin IRA-400 (hydroxide form) In methanol; water Stage #2: meso-tartaric acid In methanol; water	86%

: 147-73-9
meso-tartaric acid

: 2,3-bis(nitrooxy)succinic acid

Conditions

Conditions	Yield
With sulfuric acid; nitric acid at 38℃; for 24h;	83%

: 147-73-9
meso-tartaric acid

: 908093-98-1
diazodiphenylmethane

: 222320-54-9
bis(diphenylmethyl) meso-tartrate

Conditions

Conditions	Yield
In dichloromethane at 20℃;	82%
In methanol; chloroform Ambient temperature;

: 147-73-9
meso-tartaric acid

: 1-methylcyclohexyl {(1S,2R,4S)-2-amino-4-[(dimethylamino) carbonyl]cyclohexyl}carbamate

: C17H31N3O3*C4H6O6

Conditions

Conditions	Yield
In ethyl acetate at 20 - 25℃; for 16h;	80%

: 147-73-9
meso-tartaric acid

: 331-39-5
caffeic acid

: C22H14O14S2

Conditions

Conditions	Yield
Stage #1: caffeic acid With thionyl chloride In toluene for 4h; Reflux; Stage #2: meso-tartaric acid In toluene for 5h; Reflux;	79.7%

: 173140-90-4
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

: 312753-70-1
5,6-diethyl-2,3-dihydro-1H-inden-2-amine

: 147-73-9
meso-tartaric acid

: 5-[(R)-2-(5,6-diethylindan-2-yl-amino)-1-hydroxyethyl]-8-benzyloxy-(1H)-quinolin-2-one tartaric acid

Conditions

Conditions	Yield
Stage #1: (R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone; 5,6-diethyl-2,3-dihydro-1H-inden-2-amine In cyclohexanone at 80℃; for 6h; Stage #2: meso-tartaric acid In ethanol; cyclohexanone at 60℃; for 0.0833333h;	78.3%

...Expand

: 147-73-9
meso-tartaric acid

: 464-49-3
(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

: 149-73-5
trimethyl orthoformate

: C16H24O6

Conditions

Conditions	Yield
With sulfuric acid In methanol for 120h; Ambient temperature;	76%

...Expand

: 147-73-9
meso-tartaric acid

: 868-19-9, 22438-83-1
Sr(meso-Tar)

Conditions

Conditions	Yield
With strontium(II) acetate In water at 125℃; for 48h; Autoclave;	76%

: 147-73-9
meso-tartaric acid

: 100-46-9
benzylamine

: 1028903-71-0
(3R,4S)-1-benzyl-3,4-dihydroxypyrrolidine-2,5-dione

Conditions

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene at 190℃; for 6h; Dean-Stark;	76%
In para-xylene Reflux;

: 147-73-9
meso-tartaric acid

: dilithium(meso-tartrate)

Conditions

Conditions	Yield
With lithium acetate dihydrate In ethanol; water at 123℃; for 144h; Temperature; Autoclave;	76%

: 147-73-9
meso-tartaric acid

: 71-36-3
butan-1-ol

: 105-76-0
Dibutyl maleate

Conditions

Conditions	Yield
With per-rhenic acid In water at 170℃; for 3h; Inert atmosphere;	75%

: 147-73-9
meso-tartaric acid

: 106-65-0
Dimethyl succinate

Conditions

Conditions	Yield
With rhenium oxide and palladium co-loaded on activated carbon at 109.84℃; for 24h;	71%

: 147-73-9
meso-tartaric acid

: 3019-59-8
Weinsaeureanhydrid

Conditions

Conditions	Yield
With trifluoroacetic anhydride In dichloromethane at 20℃; for 12h;	68%

: 147-73-9
meso-tartaric acid

: 100-51-6
benzyl alcohol

: 4079-57-6, 896448-46-7
dibenzyl meso-tartrate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene Reflux; Inert atmosphere;	64%
With toluene-4-sulfonic acid In benzene

: 147-73-9
meso-tartaric acid

: 112-53-8
1-dodecyl alcohol

: 1123303-69-4
(2R,3S)-didodecyl tartarate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid at 100℃; for 2h;	64%

: silver tartrate

: (-)-(Δ)-{Co(en)2(NO2)2}Br

: 147-73-9
meso-tartaric acid

: (-)589-(.LAMDA.,.lamda.,.lamda.)-cis-bis(ethylenediamine)dinitrocobalt(III) hydrogen (+)tartrate dihydrate

Conditions

Conditions	Yield
In water stirring (-)-(.DELTA:)-(Co(en)2(NO2)2)Br, Ag2tart, and H2tart in H2O at room temp. for 20 min; reducing the vol. of filtrate by half twice yielded 2 crops, recrystn. from hot water;	62%

...Expand

: 147-73-9
meso-tartaric acid

: 78687-39-5
3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium bromide

: nicotinamide-β-D-ribofuranoside meso-hydrogen tartrate

Conditions

Conditions	Yield
Stage #1: meso-tartaric acid With triethylamine In methanol under 760.051 Torr; pH=Ca. 8; Cooling with ice; Sealed tube; Stage #2: 3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium bromide In methanol under 760.051 Torr; Heating; Sealed tube;	62%

Butanedioic acid,2,3-dihydroxy-, (2R,3S)-rel- Specification

The Butanedioic acid,2,3-dihydroxy-, (2R,3S)-rel-, with the CAS registry number 147-73-9, is also known as Butanedioic acid, 2,3-dihydroxy-, (2R,3S)- and Antiweinsaure. It belongs to the product categories of Fatty & Aliphatic Acids; Esters; Alcohols & Derivatives. Its EINECS registry number is 205-696-1. This chemical's molecular formula is C₄H₆O₆ and molecular weight is 150.09. What's more, both its IUPAC name and systematic name are the same which is called (2R,3S)-2,3-Dihydroxybutanedioic acid. In addition, This chemical can be prepared by Maleic anhydride.

Physical properties about this chemical are: (1)ACD/LogP: -1.43; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 6; (8)#H bond donors: 4; (9)#Freely Rotating Bonds: 5; (10)Polar Surface Area: 71.06 Å²; (11)Index of Refraction: 1.585; (12)Molar Refractivity: 26.69 cm³; (13)Molar Volume: 79.5 cm³; (14)Polarizability: 10.58×10^-24 cm³; (15)Surface Tension: 119.4 dyne/cm; (16)Density: 1.886 g/cm³; (17)Flash Point: 209.4 °C; (18)Enthalpy of Vaporization: 75.13 kJ/mol; (19)Boiling Point: 399.3 °C at 760 mmHg; (20)Vapour Pressure: 4.93E-08 mmHg at 25 °C.

When you are using this chemical, please be cautious about it as the following:
As a chemical, it may cause inflammation to the skin or other mucous membranes. Besides, this chemical irritates to eyes, respiratory system and skin. During using it, wear suitable protective clothing and gloves. In case of contact with eyes or skin, rinse immediately with plenty of water and seek medical advice. What's more, it must be stored in a dry, ventilated place.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(O)[C@@H](O)[C@@H](O)C(=O)O
(2) InChI: InChI=1/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)/t1-,2+
(3) InChIKey: FEWJPZIEWOKRBE-XIXRPRMCBR

Product Name

MESOTARTARIC ACID

Synthetic route

Butanedioic acid,2,3-dihydroxy-, (2R,3S)-rel- Specification

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