CAS 625-72-9 3-Hydroxybutanoic acid, (R)- (HCID 92135)

Overview

(R)-3-hydroxybutyric acid is the R-enantiomer of 3-hydroxybutyric acid. Involved in the synthesis and degradation of ketone bodies, it can be used as an energy source by the brain during hypoglycaemia, and for the synthesis of biodegradable plastics. It is a sex pheremone in the European spider Linyphia triangularis. It has a role as a pheromone, a fungal metabolite and a human metabolite. It is a 3-hydroxybutyric acid and a ketone body. It is a conjugate acid of a (R)-3-hydroxybutyrate. It is an enantiomer of a (S)-3-hydroxybutyric acid.

Names & identifiers

Preferred name: 3-Hydroxybutanoic acid, (R)-
IUPAC: (3R)-3-hydroxybutanoic acid
English name: (R)-3-Hydroxybutyric acid
Molecular formula: C4H8O3
Molecular weight: 104.1

Names & synonyms

625-72-9(R)-3-Hydroxybutyric acidButanoic acid, 3-hydroxy-, (3R)-3-D-hydroxybutyric acid3-Hydroxybutanoic acid, (R)-(-)-beta-Hydroxybutyrate, D-b-Hydroxybutyrate148ULJ1DF4EINECS 210-909-6CHEBI:170663-HYDROXYBUTYRIC ACID, (R)3-HYDROXYBUTYRIC ACID, (R)-

Show more names

d-beta-hydroxybutyrateD-3-Hydroxybutyric acid(R)-β-Hydroxybutyric acid(3R)-3-hydroxybutanoic acid(R)-3-HydroxybutyrateD(-)-3-HydroxybutyrateD-(-)-3-Hydroxybutyrate(R)-3-HydroxybuttersureLactic acid impurity 118

D-(-)-.BETA.-HYDROXYBUTYRIC ACID.BETA.-HYDROXYBUTYRIC ACID L-FORM [MI]3-hydroxy-butyrateD-(-)-beta-HYDROXYBUTYRIC ACIDRefChem:502534BETA-HYDROXYBUTYRIC ACID L-FORM210-909-6(R)-3-Hydroxybutanoic acid

Database identifiers

CAS: 625-72-9
PubChem CID: 92135
DTXSID: DTXSID3041829
ChEMBL: CHEMBL1162484
ChEBI: CHEBI:17066
UNII: 148ULJ1DF4
EC Number: 210-909-6
Nikkaji: J5.217E

Properties

Computed structural properties

XLogP: -0.5
Topological polar surface area: 57.5 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 3
Rotatable bonds: 2
Heavy atoms: 7
Formal charge: 0
Complexity: 69.3

Experimental & physicochemical properties

LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Hydroxy fatty acids [FA0105]

Melting Point49 - 50 °C

Physical DescriptionSolid

Physicochemical properties

Melting point: 49 · 49-50 °C(lit.)
Boiling point: 90 · 90-92 °C(Press: 0.08 Torr)
alpha: -25 · -25 º (C=6% IN H2O)
Density: 1.195 · 1.195±0.06 g/cm3(Predicted)
Flash point: 112 °C · 112 °C
storage temp.: 2 · Sealed in dry,2-8°C
solubility: DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly), Water (Slightly)
form: Oil to Semi-Solid
pka: 4.36 · 4.36±0.10(Predicted)
color: Colourless to Pale Yellow
optical activity: 20 · [α]20/D 25±1°, c = 6% in H2O
BRN: 1720568 · 1720568
Cosmetics Ingredients Functions: PLASTICISERHUMECTANTANTI-SEBUM
InChI: InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m1/s1
InChIKey: WHBMMWSBFZVSSR-GSVOUGTGSA-N
SMILES: C(O)(=O)C[C@H](O)C
CAS DataBase Reference: 625 · 625-72-9(CAS DataBase Reference)
FDA UNII: 148 ULJ1DF4 · 148ULJ1DF4
EPA Substance Registry System: 3 · Butanoic acid, 3-hydroxy-, (3R)- (625-72-9)
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P305+P351+P338
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36
WGK Germany: 3 · 3
F: 3 · 3-10

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): 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 82 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

F: 3-10
wgk: 3
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36
Hazard statements: H315-H319-H335
Precautionary statements: P261-P305+P351+P338

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Metabolite PathwaysFatty Acid Biosynthesis

Applications · 2 items

Description(R)-3-Hydroxybutanoic acid is a metabolite, and converted from acetoacetic acid catalyzed by 3-hydroxybutyrate dehydrogenase. It is a monomer of PHB (poly[(R)-3-hydroxybutyrate]) with wide industrial and medical applications. It can also serve as chiral precursor for synthesis of pure biodegradable PHB and its copolyesters.

Uses(R)-3-Hydroxybutyric acid may be used in the preparation of copolymers by reacting with various hydroxyalkanoic acids. It may also be used in the preparation of (3R,4R)-4-acetoxy-3-[(R)-1-(formyloxy)ethyl]-2-azetidinone.

Upstream & downstream products

Downstream products

Suppliers100 total

湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]

上海凌富药物研究有限公司+86(21)5895 0110 19945755304 · [email protected]

上海摩睿化学科技有限公司13382110328 15255501563 · [email protected]

山东泰诚生物科技有限公司18769832557 18769832557 · [email protected]

武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]

Additional notes · 1 item

DefinitionChEBI: (R)-3-hydroxybutyric acid is the R-enantiomer of 3-hydroxybutyric acid. Involved in the synthesis and degradation of ketone bodies, it can be used as an energy source by the brain during hypoglycaemia, and for the synthesis of biodegradable plastics. It is a sex pheremone in the European spider Linyphia triangularis. It has a role as a human metabolite, a pheromone and a fungal metabolite. It is a ketone body and a 3-hydroxybutyric acid. It is a conjugate acid of a (R)-3-hydroxybutyrate. It is an enantiomer of a (S)-3-hydroxybutyric acid.