3D Mol Similar

D-Valine

: Iupac Name：(2R)-2-amino-3-methylbutanoic acid; CAS No.: 640-68-6; Molecular Weight：117.14634; Modify Date.: 2022-11-29 07:57; Introduction: D-valine is the D-form of valine, being the non-proteinogenic isomer of valine. It can be supplemented into the cell culture for selectively inhibition of cell proliferation through inhibiting cells that are deficient in the enzyme D-amino acid oxidase. It has also been used to inhibit fibroblast growth while allowing the selective growth of epithelial cells. View more+

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1. Names and Identifiers

: 1.1 Name; D-Valine; 1.2 Synonyms; (2R)-2-amino-3-methylbutanoic acid (R)-(-)-2-Amino-3-methylbutyric acid (R)-(-)-VALINE (R)-2-Amino-3-methylbutanoic acid (R)-2-Amino-3-methylbutyric acid (R)-valine (R)-α-Aminoisovaleric acid, D-2-Amino-3-methylbutanoic acid (R)-α-Aminoisovaleric acid ALPHA-AMINO-ISOVALERIANIC ACID D-2-AMINO-3-METHYLBUTANOIC ACID D-2-AMINOISOVALERIC ACID D-VAL D-Valine，α-amino isovaleric acid EINECS 211-368-9 H-D-VAL-OH MFCD00064219 Valine, D-; View all

1.3 CAS No.: 640-68-6

1.4 CID: 71563

1.5 EINECS(EC#): 211-368-9

1.6 Molecular Formula: C5H11NO2 (isomer)

1.7 Inchi: InChI=1S/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t4-/m1/s1

1.8 InChIkey: KZSNJWFQEVHDMF-SCSAIBSYSA-N

1.9 Canonical Smiles: CC(C)C(C(=O)O)N

1.10 Isomers Smiles: CC(C)[C@H](C(=O)O)N

2. Properties

2.1 Density: 1.063

2.1 Melting point: 302-303℃

2.1 Boiling point: 213.6 °C at 760 mmHg

2.1 Refractive index: -27 ° (C=8, 6mol/L HCl)

2.1 Flash Point: 83 °C

2.1 Precise Quality: 117.07900

2.1 PSA: 63.32000

2.1 logP: 0.75460

2.1 Solubility: 56 g/L (20 oC)

2.2 Appearance: white crystals

2.3 Storage: Ambient temperatures.

2.4 Color/Form: White to off-white

2.5 pKa: 2.37±0.10(Predicted)

2.6 Water Solubility: H2O: 56 g/L (20 oC)

2.7 Stability: Stable under normal shipping and handling conditions.

2.8 StorageTemp: room temp

3. Use and Manufacturing

3.1 Definition: ChEBI: The D-enantiomer of valine. D-Valine Preparation Products And Raw materials Raw materials

3.2 Produe Method: 1. DL-Acetyl-methionine is used as the raw material. It undergoes acylase splitting, and further hydrochloric acid acidification to have D-valine crystals precipitated; refined product is finally obtained through recrystallization.2. The preparation method is to use 2-isopropyl-acetyl ethyl to react with benzene diazonium to get corresponding hydrazine compound, and then further reduce it to valine in zinc-ethanol solution and finally go through chemical or biological split.

3.3 Usage: 1. D-valine can be used for the synthesis of newly efficient pesticide: pyrethroids permethrin and chlorofluorocarbons amyl because of its own biochemical characteristics. The produced valine insecticide permethrin is a broad-spectrum and promising insecticide acaricide which can have effects of touch-killing and stomach poisoning through inhibiting the activity of related enzyme systems of insects. In this way, it can be used for effectively controlling of major pests including Lepidoptera and Diptera in corps such as cotton, fruit trees, and vegetables. D-valine is also widely used in biomedical research. For example, it can be used to inhibit the growth of fibroblasts, and be applied to the studies on its influence on the morphology and function of pulmonary artery endothelial cells. D-valine are also important raw materials as chiral drugs for example it may be used for the synthesis of antineoplastic drugs, anti-diabetes and its complications drugs. With the expansion of the applications fields as well as market demanding of D-valine, the preparation of D-valine will become a hot research field on amino acid.2. D-Valine is an important organic chiral source which is mainly used in fields such as chiral pharmaceuticals, chiral additive, and chiral auxiliary and other areas. It can also be used as the chiral source of chiral synthesis in the pharmaceutical industry. As an optically active organic acid, it plays an irreplaceable role in the asymmetric synthesis of certain chiral compounds. It is currently mainly used for the production of new broad-spectrum antibiotic, D-valinol, and valine protective agent during the process of peptide synthesis.3. D-valine is the intermediates for fluvalinate. 4. It is used as a pharmaceutical raw materials and pharmaceutical intermediates, and can also be used for synthetic sweeteners Alatan.5. It can also be used for biochemical research.; View all

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S22;S24/25

4.1 RIDADR: 25kgs

4.1 WGK Germany: 3

4.1 RTECS: YV9360000

4.1 Safety: Hazard Codes:Xi
Risk Statements:36/37/38
36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements:22-24/25-36-26
22:Do not breathe dust
24/25:Avoid contact with skin and eyes
36:Wear suitable protective clothing
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany:3
HS Code:29224995

4.2 Specification: white to off-white crystalline powder
Safety Statements:22-24/25-36-26
22:Do not breathe dust
24/25:Avoid contact with skin and eyes
36:Wear suitable protective clothing
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice

4.3 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YV9360000

CHEMICAL NAME :: Valine, D-

CAS REGISTRY NUMBER :: 640-68-6

LAST UPDATED :: 199706

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C5-H11-N-O2

MOLECULAR WEIGHT :: 117.17

WISWESSER LINE NOTATION :: QVYZY1&1 -D

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 6093 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Lungs, Thorax, or Respiration - dyspnea Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: ABBIA4 Archives of Biochemistry and Biophysics. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.31- 1951- Volume(issue)/page/year: 64,319,1956 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X9991 No. of Facilities: 35 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 115 (estimated) No. of Female Employees: 64 (estimated)

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

Mass spectrum (electron ionization)

7. Synthesis Route

640-68-6Total: 67 Synthesis Route

72-18-4 653 Suppliers

640-68-6 320 Suppliers

Literatures:
Journal of the Chemical Society - Series Chemical Communications, , vol. No. 1, p. 66 - 68
Yield: null

52-67-5 121 Suppliers

640-68-6 320 Suppliers

72-18-4 653 Suppliers

Literatures:
Lodemann; El-Kirdassy Wacker Arzneimittel-Forschung/Drug Research, 1980 , vol. 30, # 3 p. 395 - 397
Yield: ~45%

108-12-3 48 Suppliers

640-68-6 320 Suppliers

Literatures:
Helvetica Chimica Acta, , vol. 75, # 6 p. 1965 - 1978
Yield: null

View all

8. Precursor and Product

precursor:

4289-97-8

16935-34-5

40224-49-5

3715-29-5

42454-74-0

7146-15-8

52-67-5

24809-91-4

27675-38-3

98575-68-9

4475-96-1

1113-41-3

13474-14-1

56949-82-7

4070-48-8

53518-63-1

516-06-3

72-18-4

74784-08-0

55904-06-8

108-12-3

6070-59-3

759-05-7

View all

product :

110117-71-0

22838-58-0

90244-32-9

4216-96-0

762-75-4

1685-33-2

7146-15-8

557-24-4

4276-09-9

171567-86-5

4090-17-9

154674-67-6

143673-66-9

6893-26-1

1963-21-9

109838-85-9

868740-08-3

516-06-3

76792-22-8

82378-47-0

44976-78-5

759-05-7

View all

9. Other Information

9.0 BRN: 1721135

9.1 Description: D-valine is the D-form of valine, being the non-proteinogenic isomer of valine. It can be supplemented into the cell culture for selectively inhibition of cell proliferation through inhibiting cells that are deficient in the enzyme D-amino acid oxidase. It has also been used to inhibit fibroblast growth while allowing the selective growth of epithelial cells.

9.2 Valine: Valine is one kinds of the essential amino acids for human being with the requirement of adult males being 10mg/(kg ? d) (FAO/WHO1973). Being lack of this product can cause neurological disorders, reduction of developmental ability as well as anemia.
Valine is one of the 20 amino acids that form protein with its chemical name being 2-amino-3-methyl-butyric acid. It belongs to branched chain amino acids and is one of the eight kinds of essential amino acids and carbohydrate-producing amino acids of human body. It works together with the other two high-concentration amino acids (leucine and isoleucine) to promote the normal growth of body, tissue repair, regulate blood sugar, and provide the energy needed. When participating in intense physical activity, valine can provide extra energy to the muscles for producing glucose in order to prevent of muscle weakness. It also helps remove excess nitrogen (potentially toxic) from the liver, and transport nitrogen to all of the rest parts of the body.
Valine is an essential amino acid, which means that the human body itself cannot synthesize themselves so that it must be replenished through dietary sources. Its natural food sources include cereals, dairy products, mushrooms, mushrooms, peanuts, soy protein and meat. D-Valine is also found in some actinomyces (such as valeriana). While most people can get sufficient quantities of D-valine from the diet, however, there are still many cases about valine deficiency. Upon being lack of sufficient valine, rats get limb tremors due to disorder of the central nervous system as well as ataxia. Through dissecting slices of brain tissue, it was found about the phenomenon of the red nucleus cell degeneration. Owing to the liver function damage of patients with advanced cirrhosis of the liver, hyperinsulinemia is easy to occur, resulting in the reduction of branched chain amino acids in the blood. The ratio of branched-chain amino acids over aromatic amino acids decreases from 3.0-3.5 (normal body) to 1.0-1.5. It is common for using injection of branched chain amino acids such as valine in the treatment of liver failure, and the damage of alcoholism and drug abuse on these organs.; View all

9.3 Uses: 1. D-valine can be used for the synthesis of newly efficient pesticide: pyrethroids permethrin and chlorofluorocarbons amyl because of its own biochemical characteristics. The produced valine insecticide permethrin is a broad-spectrum and promising insecticide acaricide which can have effects of touch-killing and stomach poisoning through inhibiting the activity of related enzyme systems of insects. In this way, it can be used for effectively controlling of major pests including Lepidoptera and Diptera in corps such as cotton, fruit trees, and vegetables. D-valine is also widely used in biomedical research. For example, it can be used to inhibit the growth of fibroblasts, and be applied to the studies on its influence on the morphology and function of pulmonary artery endothelial cells. D-valine are also important raw materials as chiral drugs for example it may be used for the synthesis of antineoplastic drugs, anti-diabetes and its complications drugs. With the expansion of the applications fields as well as market demanding of D-valine, the preparation of D-valine will become a hot research field on amino acid.
2. D-Valine is an important organic chiral source which is mainly used in fields such as chiral pharmaceuticals, chiral additive, and chiral auxiliary and other areas. It can also be used as the chiral source of chiral synthesis in the pharmaceutical industry. As an optically active organic acid, it plays an irreplaceable role in the asymmetric synthesis of certain chiral compounds. It is currently mainly used for the production of new broad-spectrum antibiotic, D-valinol, and valine protective agent during the process of peptide synthesis.
3. D-valine is the intermediates for fluvalinate.
4. It is used as a pharmaceutical raw materials and pharmaceutical intermediates, and can also be used for synthetic sweeteners Alatan.
5. It can also be used for biochemical research.; View all

9.4 Chemical Properties: White crystal, m.p.> 295 °C (sublimation), [α] 25 = 27.35°; it is soluble in water and very slightly soluble in ethanol.

9.5 Production methods: 1. DL-Acetyl-methionine is used as the raw material. It undergoes acylase splitting, and further hydrochloric acid acidification to have D-valine crystals precipitated; refined product is finally obtained through recrystallization.
2. The preparation method is to use 2-isopropyl-acetyl ethyl to react with benzene diazonium to get corresponding hydrazine compound, and then further reduce it to valine in zinc-ethanol solution and finally go through chemical or biological split.

9.6 References: http://www.sigmaaldrich.com/catalog/product/sigma/v1255?lang=en®ion=US
Gilbert, S. F., and B. R. Migeon. "D-valine as a selective agent for normal human and rodent epithelial cells in culture." Cell 5.1(1975):11.
Hongpaisan, J. "Inhibition of proliferation of contaminating fibroblasts by D-valine in cultures of smooth muscle cells from human myometrium. " Cell Biology International 24.1(2000):1.

9.7 Chemical Properties: white to off-white crystalline powder

9.8 Uses: D-Valine is an isomer of the essential amino acid L-Valine. D-Valine has been used as a selective agent in epithelial cells in culture since it inhibits cells that lack the enzyme D-amino acid oxidase . D-Valine has also been shown to inhibit proliferation of contaminating fibroblasts in smooth muscle cells from human myometrium. D-Valine solution showed tumor growth inhibition and improvements of the nutritional status in AH109A hepatoma-bearing rats.

9.9 Definition: ChEBI: The D-enantiomer of valine.

9.10 General Description: L-Valine is an essential non-polar amino acid. D-Valine is the non-proteinogenic isomer of valine.

9.11 Manufacturing Info: D-Valine: ACTIVE

10. Computational chemical data

Molecular Weight: 117.14634g/mol
Molecular Formula: C₅H₁₁NO₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 117.078978594
Monoisotopic Mass: 117.078978594
Complexity: 90.4
Rotatable Bond Count: 2
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 63.3
Heavy Atom Count: 8
Defined Atom Stereocenter Count: 1
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBiMAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAHgAQCAAADSjBgAQCCABAAgAIAACQCAAAAAAAAAAAAIGAAAACABAAAAAAQAAEEAAAAAAAAAAIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

11. Question & Answer

How is D-Valine prepared and what are its applications? Jun 26 2023
Background and Overview D-Valine is an important raw material for the synthesis of pesticides, antibiotics, and physiologically active peptides. It is widely used in the fields of biology and medical ..

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