Home Cart Sign in  
Chemical Structure| 97-67-6 Chemical Structure| 97-67-6
Chemical Structure| 97-67-6

*Storage: Keep in dark place,Inert atmosphere,Room temperature.

(S)-Malic acid

CAS No.: 97-67-6

(S)-Malic acid is a naturally occurring isomer of malic acid primarily found in unripe fruits, widely used as a food additive to impart acidity.

Synonyms: (S)-Hydroxybutanedioic acid;(S)-E 296;L-Malic acid

4.5 *For Research Use Only !

Cat. No.: A266309 Purity: 98%

Change View

Size Price

USA Stock *0-1 Day

Global Stock *5-7 Days

In Stock
25g łÇʶÊÊ Inquiry Inquiry Login
100g łÇ˶ÊÊ Inquiry Inquiry Login
500g ł§Ê¶ÊÊ Inquiry Inquiry Login
1kg łÍó¶ÊÊ Inquiry Inquiry Login

Please Login or Create an Account to: See VIP prices and availability

  • 25g

    łÇʶÊÊ

  • 100g

    łÇ˶ÊÊ

  • 500g

    ł§Ê¶ÊÊ

  • 1kg

    łÍó¶ÊÊ

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

  • 1-2 Day Shipping
  • High Quality
  • Technical Support Online Technical Q&A
Product Citations

Product Details of [ 97-67-6 ]

CAS No. :97-67-6
Formula : C4H6O5
Linear Structure Formula :HOCOCH2CHOHCOOH
M.W : 134.09
SMILES Code : O=C(O)[C@@H](O)CC(O)=O
Synonyms :
(S)-Hydroxybutanedioic acid;(S)-E 296;L-Malic acid
MDL No. :MFCD00064213
InChI Key :BJEPYKJPYRNKOW-REOHCLBHSA-N
Pubchem ID :222656

Safety of [ 97-67-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Calculated chemistry of [ 97-67-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 0
Fraction Csp3 0.5
Num. rotatable bonds 3
Num. H-bond acceptors 5.0
Num. H-bond donors 3.0
Molar Refractivity 26.05
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

94.83 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

-0.01
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-1.26
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

-1.09
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

-1.37
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-1.25
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-1.0

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

0.32
Solubility 280.0 mg/ml ; 2.09 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Highly soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-0.24
Solubility 78.0 mg/ml ; 0.582 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

1.53
Solubility 4510.0 mg/ml ; 33.7 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-8.01 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

2.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.56

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.27

Application In Synthesis [ 97-67-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 97-67-6 ]

[ 97-67-6 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 68-04-2 ]
  • [ 97-67-6 ]
  • 2
  • [ 97-67-6 ]
  • [ 42890-76-6 ]
  • [ 52079-23-9 ]
  • 3
  • [ 3068-00-6 ]
  • [ 97-67-6 ]
  • benzylating reagent [ No CAS ]
  • [ 71998-69-1 ]
  • [ 71998-70-4 ]
  • 4
  • [ 97-67-6 ]
  • [ 42890-76-6 ]
  • [ 51267-44-8 ]
  • [ 52079-23-9 ]
  • 5
  • [ 97-67-6 ]
  • [ 52079-23-9 ]
YieldReaction ConditionsOperation in experiment
99.9% EXAMPLE 1 (S)-Dihydro-3-hydroxy-2 (3H)-furanone 10 g of L-(-)-malic acid is stirred in 45 ml of trifluoroacetic acid anhydride for 2 hours at 25 C. Then, it is concentrated by evaporation in a vacuum, 7 ml of methanol is added to the residue, and it is allowed to stir for 12 more hours. Then, it is concentrated by evaporation in a vacuum. The residue that is obtained is dissolved in 150 ml of absolute tetrahydrofuran. It is cooled to 0 C., and 150 ml of borane-tetrahydrofuran complex is added and allowed to stir for 2.5 more hours at 0 C. Then, 150 ml of methanol is added. It is allowed to stir for one more hour at room temperature and then concentrated by evaporation in a vacuum. The crude product that is obtained is dissolved in 80 ml of toluene. 5 g of Dowex(R) (activated, acidic) is added, and it is refluxed for one hour. Then, Dowex(R) is filtered off, and the filtrate is concentrated by evaporation in a vacuum. The crude product that is obtained (7.61 g, 99.9%) is used without purification in the next step.
  • 6
  • [ 4744-10-9 ]
  • [ 97-67-6 ]
  • [ 104-15-4 ]
  • [ 52079-23-9 ]
YieldReaction ConditionsOperation in experiment
With trifluoroacetic acid; In tetrahydrofuran; methanol; water; toluene; EXAMPLE 14 (S)-3-(Acetyloxy)-1-[4-(1-pyrrolidinyl)-2-butynyl]-2-pyrrolidinone A mixture of 60 g of (S)-malic acid, 200 ml of dimethoxypropane and 0.5 g of 4-methylphenyl sulfonic acid was stirred for 30 minutes. Water was added and the mixture was extracted four times with dichloromethane. The extracts were combined, dried and concentrated, giving 48.6 g of solid (mp 107-109 C.). This solid was dissolved in 700 ml of tetrahydrofuran, cooled to -20 C. and 160 ml of a 2.0 M solution of borane methyl sulfide complex in tetrahydrofuran was added dropwise. When the addition was complete the mixture was warmed to room temperature, heated at reflux for 1 hour, and cooled. Methanol was added and the mixture concentrated in vacuo. The residue was concentrated twice from 500 ml of methanol and once from 200 ml of toluene. The residue was diluted with dichloromethane, filtered and concentrated to 200 ml. Trifluoroacetic acid (20 ml) was added and this mixture was stirred overnight. The mixture was evaporated from three 200 ml portions of toluene. The residue was distilled at 1.0 mm, 100 C., giving 27 g of (S)-dihydro-3-hydroxy-2(3H)-furanone as a colorless oil.
  • 7
  • [ 20388-87-8 ]
  • [ 97-67-6 ]
  • (2R)-2-phenylpropylamine malate [ No CAS ]
YieldReaction ConditionsOperation in experiment
85.2% Charge 2 -phenyl- 1 -propylamine HCl (317.2 g, 1.85 moles), dry ethanol (2.0 L) and NaOH beads (75.4 g, 1.89 moles) washed with additional ethanol (500 mL) to a dry 3 -L round bottom flask under nitrogen. Stir the mixture for 1.6 hours. Filter and add a solution of L-malic acid (62.0 g, 0.462 mole, 0.25 equivalents) in ethanol (320 mL) dropwise to the yellow filtrate. Heat the solution to 75C, then stir at 75C for 30 minutes. Remove heat and allow the solution to cool slowly. Allow the resulting thick precipitate to stir overnight. Filter the precipitate, rinse with ethanol (325 mL) and dry under reduced pressure to afford (2R)-2-phenylpropylamine malate (147.6 g, 39.5%) as a white crystalline solid. Chiral GC analysis of the free base, 2 -phenyl- 1 -propylamine reveals 83.2% e.e. enriched in the R-isomer. (Configuration is assigned via spectrometric comparison with commercial 2 -phenyl- 1 -propylamine.) IH NMR (CDCI3, 300 MHz) delta 7.32 (m, 2H), 7.21 (m, 3H), 2.86 (m, 2H), 2.75 (m, IH), 1.25 (d, 3H, J=6.9), 1.02 (br s, 2H).Heat a slurry of (2R)-2-phenylpropylamine malate (147.1 g, 83.2% e.e.) in 1325 mL ethanol and 150 mL deionized water to reflux (approximately 79.2 0C) until the solids dissolve. Allow the homogeneous solution to slowly cool with stirring overnight. Cool the precipitate (0 0C to 5 0C) and filter. Collect solids, rinse with ethanol (150 mL), and dry at 35C to afford (2R)-2-phenylpropylamine malate (125.3 g, 85.2% recovery) as a white powder. Chiral GC analysis of the free base, (2R)-2-phenylpropylamine, reveals 96.7% e.e. enriched in the R-isomer. IH NMR (CD3OD, 300 MHz) delta 7.32 (m, 10 H), 4.26 (dd, IH, J=3.6, 9.9), 3.08 (m, 6H), 2.72 (dd, IH, J=9.3, 15.3), 2.38 (dd, IH, J=9.3, 15.6), 1.33 (d, 6H, J=6.6).
  • 8
  • [ 97-67-6 ]
  • [ 173334-57-1 ]
  • [ 1327153-72-9 ]
YieldReaction ConditionsOperation in experiment
63.3% In water; for 0.5h;Product distribution / selectivity; Example 13<strong>[173334-57-1]Aliskiren</strong> MalateA solution of 109.8 mg (0. 8192 mmol) L-malic acid in 2 ml water was added to 452 mg (0.819 mmol) <strong>[173334-57-1]Aliskiren</strong> free base and the resulting mixture was shaken well for 30 min resulting in a milky solution. This was frozen, using liquid nitrogen, and was lyophilized for 3 h to yield 356 mg (63.3 %) of a white solid.LCMS purity: 99.51 %. Melting point: 63 C - 69 C.DSC shows a very broad endotherm at 177.6 and 193.8 C.IR: 2959.9, 2874.6, 1720.1 , 1659.3, 1588.7, 1516.1 and 1474.3 cm 1.
In ethanol; dichloromethane; at 20℃; for 24h; Example 24: Preparation of aliskiren L-malic acid salt <strong>[173334-57-1]Aliskiren</strong> (1.6 g, 2.9 mmol) was dissolved in dichloromethane (10 mL), and L-malic acid (0.194 g, 1.45 mmol) in ethanol (1 mL) was added while stirring. The solution was stirred at room temperature for 24 h. Then, solvent was evaporated in vacuum, and the product was dried under vacuum at 30C over night. Mp = 79.9-85C XRPD: amorphous
  • 9
  • [ 97-67-6 ]
  • [ 173334-57-1 ]
  • (2S),(4S),(5S),(7S)-N-(3-amino-2,2-dimethyl-3-oxopropyl)-2,7-di(1-methylethyl)-4-hydroxy-5-amino-8-[4-methoxy-3-(3-methoxy-propoxy)phenyl]-octanamide hemi(L-malate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
91.7% In water; for 0.5h;Product distribution / selectivity; Example 25<strong>[173334-57-1]Aliskiren</strong> L-Malate 2 : 1A solution of 0.127 g (0.951 mmol) L-malic acid in 15 ml water was added to 1.05 g (1.903 mmol) <strong>[173334-57-1]Aliskiren</strong> free base and stirred slowly for 30 min to obtain a turbid solution. By swirling the flask and freezing at -40C (using a Julabo chiller), the solution was converted into a thin film and subsequently the flask was connected to a freeze drier (conditions: vacuum: 18 mTorr, condenser temperature -104.2 C) for 4 h to obtain solid. Yield = 1 .08 g (91.7 %).DSC showed two merging endothermic peaks at 49.1 , 53.96 (due to water) and a broad endothermic peak at 178.6 C.
  • 10
  • [ 97-67-6 ]
  • [ 500287-72-9 ]
  • rilpivirine L-malate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; at 45℃; <strong>[500287-72-9]Rilpivirine</strong> base Form II (0.30 g, 0.82 mmol) was dissolved in THF (6 mL) at 45C. L-Malic acid (121 mg, 0.90 mmol, 1.1 eq) was dissolved in THF (3 mL) at room temperature and the resulting solution was then added portion- wise to the solution containing <strong>[500287-72-9]Rilpivirine</strong> base at 45C with stirring. The reaction mixture was removed from the heat source and stirring was continued at room temperature for about 17 h. A precipitate formed and was isolated by filtration to give <strong>[500287-72-9]Rilpivirine</strong> L-malate Form 1. Drying of this material in a vacuum oven at 50C for 18 h afforded the same polymorphic form as was identified prior to drying.
  • 11
  • [ 6490-42-2 ]
  • [ 97-67-6 ]
  • C6H8N2O2*C4H6O5 [ No CAS ]
 

Related Products

Technical Information

Categories

Related Functional Groups of
[ 97-67-6 ]

Aliphatic Chain Hydrocarbons

Chemical Structure| 636-61-3

A100216 [636-61-3]

(R)-2-Hydroxysuccinic acid

Similarity: 1.00

Chemical Structure| 133-37-9

A103267 [133-37-9]

(2R,3R)-rel-2,3-Dihydroxysuccinic acid

Similarity: 1.00

Chemical Structure| 87-69-4

A144400 [87-69-4]

(2R,3R)-2,3-Dihydroxysuccinic acid

Similarity: 1.00

Chemical Structure| 147-71-7

A411816 [147-71-7]

(2S,3S)-2,3-Dihydroxysuccinic acid

Similarity: 1.00

Chemical Structure| 778571-57-6

A109634 [778571-57-6]

Magnesium (2R,3S)-2,3,4-trihydroxybutanoate

Similarity: 0.96

Alcohols

Chemical Structure| 636-61-3

A100216 [636-61-3]

(R)-2-Hydroxysuccinic acid

Similarity: 1.00

Chemical Structure| 133-37-9

A103267 [133-37-9]

(2R,3R)-rel-2,3-Dihydroxysuccinic acid

Similarity: 1.00

Chemical Structure| 87-69-4

A144400 [87-69-4]

(2R,3R)-2,3-Dihydroxysuccinic acid

Similarity: 1.00

Chemical Structure| 147-71-7

A411816 [147-71-7]

(2S,3S)-2,3-Dihydroxysuccinic acid

Similarity: 1.00

Chemical Structure| 778571-57-6

A109634 [778571-57-6]

Magnesium (2R,3S)-2,3,4-trihydroxybutanoate

Similarity: 0.96

Carboxylic Acids

Chemical Structure| 636-61-3

A100216 [636-61-3]

(R)-2-Hydroxysuccinic acid

Similarity: 1.00

Chemical Structure| 133-37-9

A103267 [133-37-9]

(2R,3R)-rel-2,3-Dihydroxysuccinic acid

Similarity: 1.00

Chemical Structure| 87-69-4

A144400 [87-69-4]

(2R,3R)-2,3-Dihydroxysuccinic acid

Similarity: 1.00

Chemical Structure| 147-71-7

A411816 [147-71-7]

(2S,3S)-2,3-Dihydroxysuccinic acid

Similarity: 1.00

Chemical Structure| 3347-90-8

A186753 [3347-90-8]

(S)-2-Hydroxybutanoic acid

Similarity: 0.91