CAS 640-68-6 D-Valine (HCID 71563)

Overview

D-valine is the D-enantiomer of valine. It is a D-alpha-amino acid and a valine. It is a conjugate base of a D-valinium. It is a conjugate acid of a D-valinate. It is an enantiomer of a L-valine. It is a tautomer of a D-valine zwitterion.

Names & identifiers

Preferred name: D-Valine
IUPAC: (2R)-2-amino-3-methylbutanoic acid
English name: D-Valine
Molecular formula: C5H11NO2
Molecular weight: 117.15

Names & synonyms

D-Valine640-68-6(R)-Valine(2R)-2-amino-3-methylbutanoic acidValine, D-D-valin(R)-2-Amino-3-methylbutyric acidEINECS 211-368-9NSC 20654DTXSID0046064D-2-Amino-3-methylbutanoic acidD-(-)-VALINE

Show more names

ValD-VALH-D-VAL-OH(R)-2-AMINO-3-METHYLBUTANOIC ACIDValnemulin hydrochloride EP Impurity Ddextro-valineD-Valine, 97+%

Y14I1443URNSC-20654VALINE, (-)-DTXCID8026064CHEBI:27477D-2-amino-3-methylbutyric acid2-Amino-3-methylbutanoic acid(D)(R)Valine

Database identifiers

CAS: 640-68-6
PubChem CID: 71563
DTXSID: DTXSID0046064
ChEMBL: CHEMBL1232398
ChEBI: CHEBI:27477
UNII: Y14I1443UR
EC Number: 211-368-9
Nikkaji: J9.198G

Properties

Computed structural properties

XLogP: -2.3
Topological polar surface area: 63.3 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 3
Rotatable bonds: 2
Heavy atoms: 8
Formal charge: 0
Complexity: 90.4

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Amino Acids and Derivatives

Physical DescriptionWhite powder; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point: 295 °C · >295 °C (subl.)(lit.)
alpha: -27.5 · -27.5 º (c=5, 5N HCl)
Boiling point: 213.6 · 213.6±23.0 °C(Predicted)
Density: 1.2 · 1.2000 (estimate)
refractive index: -27 ° · -27 ° (C=8, 6mol/L HCl)
storage temp.: room temp
solubility: 56 g/L · 56 g/L (20°C)
pka: 2.37 · 2.37±0.10(Predicted)
form: Crystalline Powder
color: White to off-white
biological source: synthetic (organic)
optical activity: 23 · [α]23/D 32.0 to 24.0°, c = 8 in 6 M HCl
Water Solubility: 56 g/L · 56 g/L (20 ºC)
BRN: 1721135 · 1721135
Cosmetics Ingredients Functions: SKIN CONDITIONINGANTISTATICHAIR CONDITIONINGFRAGRANCE
InChI: 1S/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t4-/m1/s1
InChIKey: KZSNJWFQEVHDMF-SCSAIBSYSA-N
SMILES: CC(C)[C@@H](N)C(O)=O
LogP: 0.289 · 0.289 (est)
CAS DataBase Reference: 640 · 640-68-6(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 14 I1443UR · Y14I1443UR
NIST Chemistry Reference: 2 · 2-Amino-3-methylbutanoic acid(D)(640-68-6)
EPA Substance Registry System: D-Valine (640-68-6)
UNSPSC Code: 12352209 · 12352209
NACRES: 75 · NA.75
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P271-P280
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 22 · 22-24/25-36-26
WGK Germany: 3 · 3
RTECS: 9360000 · YV9360000
TSCA: TSCA listed
HS Code: 29224995 · 29224995
Storage Class: 11 · 11 - Combustible Solids
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 87.5% (7 of 8) of all reports.

Warning

H315 (12.5%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 8 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

Chemical: D-Valine

Status: Active Update: 17-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/25830

D-Valine: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - D-Valine: Environment tier I assessment

Hazards SummaryMay cause irritation; [Sigma-Aldrich MSDS]

Hazard Classes and CategoriesSkin Irrit. 2 (12.5%)

Safety data

wgk: 3
tsca: TSCA listed
rtecs: YV9360000
hs_code: 29224995
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 22-24/25-36-26
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319-H335
REACH Registrations: Active
Precautionary statements: P261-P271-P280

Chemistry & industry

Uses & manufacturing

UsesValine is an essential amino acid; [Merck Index]

General Manufacturing InformationD-Valine: ACTIVE

Applications · 3 items

DescriptionD-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.

Uses1.D-valine can be used for the synthesis of newly efficient pesticide: pyrethroids permethrin and chlorofluorocarbons amyl because of its own biochemical characteristics. 2.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. 3.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. 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, antineoplastic drugs, anti-diabetes and its complications drugs.

UsesD-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.

Upstream & downstream products

Upstream raw materials

Downstream products

(R)-2,5-Dihydro-3,6-diethoxy-2-isopropylpyrazine (R)-3-Isopropyl-2,5-piperazinedione (R)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine D(-)-Glutamic acid D-Valine, N-[(4-bromophenyl)sulfonyl]-

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]

北京华美互利生物化工010-56205725 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

黄冈森阳化工有限公司0713-8205211 17671088222 · [email protected]

Additional notes · 1 item

DefinitionChEBI: D-valine is the D-enantiomer of valine. It is a valine and a D-alpha-amino acid. It is a conjugate base of a D-valinium. It is a conjugate acid of a D-valinate. It is an enantiomer of a L-valine. It is a tautomer of a D-valine zwitterion.