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(2R)-2-ammonio-3-methylbutanoate

HCID 6971095
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
640-68-6
Standard SMILES
CC(C)[C@@H]([NH3+])C(=O)[O-]
InChIKey
KZSNJWFQEVHDMF-SCSAIBSYSA-N
Molecular formula
C5H11NO2
Average molar mass
117.15 g/mol
Monoisotopic mass
117.07897859

Overview

D-valine zwitterion is a D-alpha-amino acid zwitterion that is D-valine in which a proton has been transferred from the carboxy group to the amino group. It is the major species at pH 7.3. It is a tautomer of a D-valine.

Names & identifiers

Preferred name
(2R)-2-ammonio-3-methylbutanoate
IUPAC
(2R)-2-azaniumyl-3-methylbutanoate
English name
D-Valine
Molecular formula
C5H11NO2
Molecular weight
117.15

Names & synonyms

(2R)-2-ammonio-3-methylbutanoateD-valine zwitterionCHEBI:74338ValD-VALH-D-VAL-OH(R)-2-AMINO-3-METHYLBUTANOIC ACIDValnemulin hydrochloride EP Impurity DD-VALINENSC 20654Valine, D-dextro-valine
Show more names
D-Valine, 97+%

Database identifiers

CAS
640-68-6
PubChem CID
6971095
ChEBI
CHEBI:74338

Properties

Computed structural properties

XLogP
-1.6
Topological polar surface area
67.8 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
8
Formal charge
0
Complexity
84.9

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

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

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

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

ValineDL-ValineEthyl 2-isopropylacetoacetate

Downstream products

(R)-2,5-Dihydro-3,6-diethoxy-2-isopropylpyrazine

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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
(R)-3-Isopropyl-2,5-piperazinedione
(R)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine
D(-)-Glutamic acid
D-Valine, N-[(4-bromophenyl)sulfonyl]-
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.