Butanedioic acid,2-hydroxy-2-methyl-, (2S)- supplier

Name
(S)-(+)-CITRAMALIC ACID
EINECS 228-350-1
CAS No. 6236-09-5
Article Data18
CAS DataBase
Density 1.513 g/cm³
Solubility
Melting Point 109-111 °C(lit. )
Formula C₅H₈O₅
Boiling Point 295.2 °C at 760 mmHg
Molecular Weight 148.116
Flash Point 146.6 °C
Transport Information
Appearance white fine crystalline powder
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Butanedioicacid, 2-hydroxy-2-methyl-, (S)-;Malic acid, 2-methyl-, (S)-(+)- (8CI);(+)-Citramalic acid;(+)-Methylmalic acid;(S)-(+)-Citramalic acid;(S)-Citramalic acid;2S-Methylmalic acid;L-Citramalic acid;
PSA 94.83000
LogP -0.70330

Synthetic route

: 93239-42-0
(R)-4-methyl-4-(trichloromethyl)-2-oxetanone

: 6236-09-5
(S)-citramalic acid

Conditions

Conditions	Yield
With sodium hydroxide In water 1.) 5 deg C; 2.) room temperature;	96%
With sodium hydroxide at 20℃; Hydrolysis;

: (2'R,4'S)-2-<2'-(tert-Butyl)-4'-methyl-1',3'-dioxolan-4'-yl>essigsaeure

: 6236-09-5
(S)-citramalic acid

Conditions

Conditions	Yield
With hydrogenchloride at 80℃; for 19h;	80%

: 498-24-8
Mesaconic acid

: 6236-09-5
(S)-citramalic acid

Conditions

Conditions	Yield
With formaldehyd; TETRACYCLINE; paraquat dichloride In water at 37℃; for 24h; Clostridium formicoaceticum, phosphate buffer;	69.8%
mit Hilfe eines Mesaconase-Praeparats;

: 597-44-4
2-hydroxy-2-methylbutane-1,4-dioic acid

: 6236-09-5
(S)-citramalic acid

Conditions

Conditions	Yield
With strychnidin-10-one
With water; brucine

: 32814-40-7
S-(+)-Methyl-γ-iodo-β-carbomethoxy-β-hydroxy-butyrat

: 6236-09-5
(S)-citramalic acid

Conditions

Conditions	Yield
(i) NaSH, H2S, EtOH, (ii) Raney-Ni, acetone, (iii) aq. HCl; Multistep reaction;

: 92572-49-1
<(2S,4S)-2-tert-butyl-4-methyl-5-oxo-1,3-dioxolan-4-yl>acetic acid

: 6236-09-5
(S)-citramalic acid

: (2R,3S,5S)-5-((R)-1,2-Dihydroxy-ethyl)-3-methyl-tetrahydro-furan-2,3-diol

: 6236-09-5
(S)-citramalic acid

Conditions

Conditions	Yield
With potassium hydroxide; potassium permanganate 1.) water, 4-5 deg C, 1 h; Yield given. Multistep reaction;

: (S)-2-Hydroxy-2-methyl-succinic acid 1-((1S,2R)-2-phenyl-cyclohexyl) ester

: 6236-09-5
(S)-citramalic acid

Conditions

Conditions	Yield
With potassium hydroxide In tetrahydrofuran at 60℃; for 24h;

: 32150-78-0
(4S)-(+)-4-methylmuconolactone

: 6236-09-5
(S)-citramalic acid

Conditions

Conditions	Yield
With nitric acid; ozone 1.) CH2Cl2, -70 deg C; 2.) H2O, 90 deg C; Multistep reaction;

: 197069-14-0
1-benzyl hydrogen 2-hydroxy-2-methylbutanedioate

: 6236-09-5
(S)-citramalic acid

Conditions

Conditions	Yield
With potassium hydroxide Hydrolysis;

: (2E,4E,7S,8E,10E,12E,14S)-7,9,13,17-tetramethyl-7,14-dihydroxy-2,4,8,10,12,16-octadecahexaenoic acid

A: 6236-09-5
(S)-citramalic acid

B: 144-62-7
oxalic acid

C: 64-19-7
acetic acid

D: 127-17-3
2-oxo-propionic acid

Conditions

Conditions	Yield
With ozone In dichloromethane at -78℃; for 0.0833333h; Further byproducts given. Title compound not separated from byproducts;

...Expand

: (2E,4E,7S,8E,10E,12E,14S)-7,9,13,17-tetramethyl-7,14-dihydroxy-2,4,8,10,12,16-octadecahexaenoic acid

A: 6236-09-5
(S)-citramalic acid

B: 141-82-2
malonic acid

C: 144-62-7
oxalic acid

D: 127-17-3
2-oxo-propionic acid

Conditions

Conditions	Yield
With ozone In dichloromethane at -78℃; for 0.0833333h; Further byproducts given. Title compound not separated from byproducts;

...Expand

: 14-O-β-D-glucopyranosyl-(2E,4E,7S,8E,10E,12E,14R)-7,9,13,17-tetramethyl-7,14-dihydroxy-2,4,8,10,12,16-octadecahexaenoic acid

A: 6236-09-5
(S)-citramalic acid

B: 144-62-7
oxalic acid

C: 64-19-7
acetic acid

D: 127-17-3
2-oxo-propionic acid

Conditions

Conditions	Yield
With ozone In dichloromethane at -78℃; for 0.0833333h; Further byproducts given. Title compound not separated from byproducts;

...Expand

: 14-O-β-D-glucopyranosyl-(2E,4E,7S,8E,10E,12E,14R)-7,9,13,17-tetramethyl-7,14-dihydroxy-2,4,8,10,12,16-octadecahexaenoic acid

A: 6236-09-5
(S)-citramalic acid

B: 141-82-2
malonic acid

C: 64-19-7
acetic acid

D: 127-17-3
2-oxo-propionic acid

Conditions

Conditions	Yield
With ozone In dichloromethane at -78℃; for 0.0833333h; Further byproducts given. Title compound not separated from byproducts;

...Expand

: 14-O-α-D-glucopyranosyl-(2E,4E,7S,8E,10E,12E,14S)-7,9,13,17-tetramethyl-7,14-dihydroxy-2,4,8,10,12,16-octadecahexaenoic acid

A: 6236-09-5
(S)-citramalic acid

B: 144-62-7
oxalic acid

C: 64-19-7
acetic acid

D: 127-17-3
2-oxo-propionic acid

Conditions

Conditions	Yield
With ozone In dichloromethane at -78℃; for 0.0833333h; Further byproducts given. Title compound not separated from byproducts;

...Expand

: 14-O-α-D-glucopyranosyl-(2E,4E,7S,8E,10E,12E,14S)-7,9,13,17-tetramethyl-7,14-dihydroxy-2,4,8,10,12,16-octadecahexaenoic acid

A: 6236-09-5
(S)-citramalic acid

B: 141-82-2
malonic acid

C: 144-62-7
oxalic acid

D: 127-17-3
2-oxo-propionic acid

Conditions

Conditions	Yield
With ozone In dichloromethane at -78℃; for 0.0833333h; Further byproducts given. Title compound not separated from byproducts;

...Expand

: 104194-10-7
(2R,5S)-2-(tert-Butyl)-5-methyl-5-(2'-nitroethyl)-1,3-dioxolan-4-on

: 6236-09-5
(S)-citramalic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / NaNO2, BuNO2 / dimethylsulfoxide / 16 h / Ambient temperature 2: 80 percent / 2 N HCl / 19 h / 80 °C View Scheme

: 58109-21-0, 58109-22-1, 58109-23-2
methyl 5,6-O-cyclohexylidene-3-deoxy-2-C-methyl-β-D-arabino-hexofuranoside

: 6236-09-5
(S)-citramalic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Dowex 50W-X8 / dioxane; H2O / 1 h / 90 °C 2: 1.) KOH, KMnO4 / 1.) water, 4-5 deg C, 1 h View Scheme

: 32814-34-9
L-2-Hydroxyparaconic acid

: 6236-09-5
(S)-citramalic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 2: NaI / acetone 3: (i) NaSH, H2S, EtOH, (ii) Raney-Ni, acetone, (iii) aq. HCl View Scheme

: 32814-35-0, 143954-94-3
R-(+)-Methyl-γ-(p-toluolsulfonyloxy)-β-carbomethoxy-β-hydroxybutyrat

: 6236-09-5
(S)-citramalic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaI / acetone 2: (i) NaSH, H2S, EtOH, (ii) Raney-Ni, acetone, (iii) aq. HCl View Scheme

: 186581-53-3, 908094-01-9
diazomethane

: 6236-09-5
(S)-citramalic acid

: 38574-61-7
(R)-2-hydroxy-2-methyl-butan-1,4-dioic acid dimethyl ester

Conditions

Conditions	Yield
In methanol	100%
In methanol; diethyl ether at 0℃;	94%

: 6236-09-5
(S)-citramalic acid

: 684-16-2
Hexafluoroacetone

: 184305-30-4
[(5S)-2,2-Bis(trifluoromethyl)-5-methyl-4-oxo-1,3-dioxolan-5-yl] acetic acid

Conditions

Conditions	Yield
In dimethyl sulfoxide at 20℃;	89%
In dimethyl sulfoxide	87%
In dimethyl sulfoxide at 20℃;	87%
In dimethyl sulfoxide at 20℃; Cyclization;

: 115-17-3
bromal

: 6236-09-5
(S)-citramalic acid

: 1108205-25-9
[(4S)-4-methyl-5-oxo-2-(tribromomethyl)-1,3-dioxolan-4-yl]acetic acid

Conditions

Conditions	Yield
With sulfuric acid; acetic acid at 0℃; for 2h;	87%

: 115-17-3
bromal

: 6236-09-5
(S)-citramalic acid

: [(4S)-4-methyl-5-oxo-2-(tribromomethyl)-1,3-dioxolan-4-yl]acetic acid

Conditions

Conditions	Yield
With sulfuric acid; acetic acid at 0℃; for 2h;	77%

: 6236-09-5
(S)-citramalic acid

: 60299-29-8
(S)-(-)-2-Methylbutane-1,2,4-triol

Conditions

Conditions	Yield
Stage #1: (S)-citramalic acid With methanol; sulfuric acid Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran Further stages.;	72%
With dimethylsulfide borane complex In tetrahydrofuran; methanol at 0 - 60℃; for 1.5h;
Multi-step reaction with 2 steps 1: CH2Cl2; ethanol 2: LiAlH4 / tetrahydrofuran / Heating View Scheme
Multi-step reaction with 2 steps 2: 93 percent / lithium aluminium hydride / tetrahydrofuran / 18 h / Heating View Scheme

: nickel(II) chloride hexahydrate

: 6236-09-5
(S)-citramalic acid

: 7732-18-5
water

: diaqua((S)-2-hydroxy-2-methyl-butanedioate)nickel(II)

Conditions

Conditions	Yield
With KOH In ethanol; water High Pressure; heated at 180°C for 2 d; cooled, ppt. washed and rinsed (water, ethanol); elem. anal., TGA;	71%

...Expand

: cobalt(II) chloride hexahydrate

: 6236-09-5
(S)-citramalic acid

: 7732-18-5
water

: diaqua((S)-2-hydroxy-2-methyl-butanedioate)cobalt(II)

Conditions

Conditions	Yield
With KOH In ethanol; water High Pressure; heated at 180°C for 2 d; cooled, ppt. washed and rinsed (water, ethanol); elem. anal., TGA;	67%

...Expand

: manganese(II) chloride tetrahydrate

: 6236-09-5
(S)-citramalic acid

: 7732-18-5
water

: diaqua((S)-2-hydroxy-2-methyl-butanedioate)manganese(II)

Conditions

Conditions	Yield
With KOH In ethanol; water High Pressure; heated at 180°C for 2 d; cooled, ppt. washed and rinsed (water, ethanol); elem. anal., TGA;	59%

...Expand

: 6236-09-5
(S)-citramalic acid

: 300-85-6, 625-71-8
3-Hydroxybutyric acid

Conditions

Conditions	Yield
With 2,6-dimethylpyridine; 4,4'-dichlorodiphenyl disulfide; 10-methyl-9-(2,4,6-trimethylphenyl) acridinium tetrafluoroborate In 1,2-dichloro-ethane at 20℃; for 14h; Irradiation; Inert atmosphere; regioselective reaction;	52%

: 366-18-7
[2,2]bipyridinyl

: 12440-03-8, 772292-34-9, 121437-28-3, 22534-68-5
vanadium(IV) oxide sulfate hydrate

: 6236-09-5
(S)-citramalic acid

: [ΔVO(S-Hcitmal)(2,2′-bipyridine)]*2H2O

Conditions

Conditions	Yield
With potassium hydroxide In ethanol; water	39%

...Expand

: 6236-09-5
(S)-citramalic acid

: C20H23F2N3O2*(x)ClH

: (S)-4-(3-((2-(difluoromethoxy)-6-methylpyridin-3-yl)carbamoyl)-3-(2-isopropylphenyl)azetidin-1-yl)-2-hydroxy-2-methyl-4-oxobutanoic acid

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	29%

: 64-17-5
ethanol

: 6236-09-5
(S)-citramalic acid

: 42108-93-0
(S)-(+)-Citramalsaeure-diethylester

Conditions

Conditions	Yield
With sulfuric acid

: 67-56-1
methanol

: 6236-09-5
(S)-citramalic acid

: 38574-61-7
(R)-2-hydroxy-2-methyl-butan-1,4-dioic acid dimethyl ester

Conditions

Conditions	Yield
With hydrogenchloride at 55℃; for 48h;
With hydrogenchloride Esterification;	58.7 mg
With thionyl chloride
With thionyl chloride at 20℃;
With thionyl chloride at 20℃; for 3h; Cooling;

: 6236-09-5
(S)-citramalic acid

: 62875-07-4
(+/-)-2-methylbutane-1,2,4-triol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 2h; Heating;

Butanedioic acid,2-hydroxy-2-methyl-, (2S)- Specification

The Butanedioic acid, 2-hydroxy-2-methyl-, (2S)-, with the CAS registry number of 6236-09-5, is also known as (S)-(+)-Citramalic acid and L-(+)-2-Methylmalic acid. Its EINECS registry number is 228-350-1. This chemical's molecular formula is C₅H₈O₅ and molecular weight is 148.11. What's more, its IUPAC name is (2S)-2-Hydroxy-2-methylbutanedioic acid.

Physical properties about Butanedioic acid, 2-hydroxy-2-methyl-, (2S)- are: (1)ACD/LogP: -0.91; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -4.03; (4)ACD/LogD (pH 7.4): -5.65; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 5; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 61.83 Å²; (13)Index of Refraction: 1.521; (14)Molar Refractivity: 29.84 cm³; (15)Molar Volume: 97.8 cm³; (16)Polarizability: 11.83×10^-24 cm³; (17)Surface Tension: 73.4 dyne/cm; (18)Density: 1.513 g/cm³; (19)Flash Point: 146.6 °C; (20)Enthalpy of Vaporization: 62.05 kJ/mol; (21)Boiling Point: 295.2 °C at 760 mmHg; (22)Vapour Pressure: 0.000161 mmHg at 25 °C; (23)Melting Point: 109-111 °C(lit. ).

When you are using this chemical, please be cautious about it as the following:
As a chemical, it is irritating to eyes, respiratory system and skin. In addition, this chemical may cause inflammation to the skin or other mucous membranes. During using it, wear suitable protective clothing. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(O)C(O)(C)CC(=O)O
(2) InChI: InChI=1/C5H8O5/c1-5(10,4(8)9)2-3(6)7/h10H,2H2,1H3,(H,6,7)(H,8,9)
(3) InChIKey: XFTRTWQBIOMVPK-UHFFFAOYAT

Product Name

(S)-(+)-CITRAMALIC ACID

Synthetic route

Butanedioic acid,2-hydroxy-2-methyl-, (2S)- Specification

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