(R)-3-Hydroxybuttersure
3-Hydroxybutanoic acid, (R)-
Grundinformationen
- CAS
625-72-9- Standard-SMILES
C[C@@H](O)CC(=O)O- InChIKey
WHBMMWSBFZVSSR-GSVOUGTGSA-N- Summenformel
- C4H8O3
- Durchschnittliche Molmasse
- 104,1 g/mol
- Monoisotopische Masse
- 104,04734412
Überblick
(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.
Namen und Bezeichner
- Bevorzugter Name
- 3-Hydroxybutanoic acid, (R)-
- IUPAC
- (3R)-3-hydroxybutanoic acid
- Lokaler Name
- (R)-3-Hydroxybuttersure
- Englischer Name
- (R)-3-Hydroxybutyric acid
- Summenformel
- C4H8O3
- Molmasse
- 104.1
Namen und Synonyme
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)-
Weitere Namen anzeigen
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
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,5
- Polarare Oberfläche (TPSA)
- 57,5 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 7
- Formalladung
- 0
- Komplexität
- 69,3
Experimentelle und physikochemische Eigenschaften
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Hydroxy fatty acids [FA0105]
Melting Point49 - 50 °C
Physical DescriptionSolid
Physikochemische Eigenschaften
- Schmelzpunkt
- 49 · 49-50 °C(lit.)
- Siedepunkt
- 90 · 90-92 °C(Press: 0.08 Torr)
- Dichte
- 1.195 · 1.195±0.06 g/cm3(Predicted)
- Flammpunkt
- 112 °C · 112 °C
- storage temp.
- 2 · Sealed in dry,2-8°C
- Löslichkeit
- DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly), Water (Slightly)
- Aggregatzustand
- Oil to Semi-Solid
- pka
- 4.36 · 4.36±0.10(Predicted)
- Farbe
- Colourless to Pale Yellow
- BRN
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
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.
Gefahrenhinweise
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Sicherheitsdaten
- F
- 3-10
- wgk
- 3
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26-36
Chemie und Industrie
Pharmakologische Informationen
Cellular LocationsCytoplasm
Metabolite PathwaysFatty Acid Biosynthesis
Anwendungen
Beschreibung(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.
Verwenden(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.
Vor- und nachgelagerte Produkte
Nachgelagerte Produkte
Ergänzende Hinweise
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.
Zugehörige Reaktionen
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