CAS 7331-52-4 3-Hydroxybutyrolactone, (3S)- (HCID 7269389)

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Basic information

CAS: 7331-52-4
Standard SMILES: O=C1C[C@H](O)CO1
InChIKey: FUDDLSHBRSNCBV-VKHMYHEASA-N
Molecular formula: C4H6O3
Average molar mass: 102.09 g/mol
Monoisotopic mass: 102.03169405

Names & identifiers

Preferred name: 3-Hydroxybutyrolactone, (3S)-
IUPAC: (4S)-4-hydroxyoxolan-2-one
English name: (S)-3-Hydroxy-gamma-butyrolactone
Molecular formula: C4H6O3
Molecular weight: 102.09

Names & synonyms

7331-52-4(S)-3-Hydroxy-gamma-butyrolactone(4S)-4-hydroxyoxolan-2-one(S)-beta-Hydroxy-gamma-butyrolactone3-Hydroxybutyrolactone, (3S)-2(3H)-Furanone, dihydro-4-hydroxy-, (4S)-2LIE7314JHDTXSID60428483EC 434-990-43-HYDROXYBUTYROLACTONE, (-)-(S)-3-HYDROXY-.GAMMA.-BUTYROLACTONE(S)-.BETA.-HYDROXY-.GAMMA.-BUTYROLACTONE

Show more names

(S)-4-Hydroxydihydrofuran-2(3H)-one(s)-(-)-á-hydroxy--4-Hydroxydihydrofuran-2(3H)(S)-3-Hydroxy-γ-butyrolactone(S)-(-)-3-HYDROXYBUTYROLACTONE(S)-(-)-3-HYDROXY-GAMMA-BUTYROLACTONE2(3H)-FURANONE, DIHYDRO-4-HYDROXY-, (S)2(3H)-FURANONE, DIHYDRO-3-HYDROXY-, (S)(S)-3-Hydroxy-gamma-Levetiracetam Impurity 65

(S)-(-)-.BETA.-HYDROXY-.GAMMA.-BUTYROLACTONEBUTYRIC ACID, 3,4-DIHYDROXY-, .GAMMA.-LACTONE, D-GLYCERO-RefChem:502537DTXCID30379317(s)-(-)-beta-hydroxy-gamma-butyrolactoneBUTYRIC ACID, 3,4-DIHYDROXY-, GAMMA-LACTONE, D-GLYCERO-434-990-4623-293-2

Database identifiers

CAS: 7331-52-4
PubChem CID: 7269389
DTXSID: DTXSID60428483
UNII: 2LIE7314JH
EC Number: 434-990-4、623-293-2
Nikkaji: J517.046J

Properties

Computed structural properties

XLogP: -0.8
Topological polar surface area: 46.5 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 3
Rotatable bonds: 0
Heavy atoms: 7
Formal charge: 0
Complexity: 88.9

Experimental & physicochemical properties

SpringerMaterials PropertiesChemical shift

Physicochemical properties

Boiling point: 98 · 98-100 °C0.3 mm Hg(lit.)
Density: 1.241 g/mL · 1.241 g/mL at 25 °C(lit.)
refractive index: 20 · n20/D 1.464(lit.)
Flash point: 230 °F · >230 °F
storage temp.: 2 · Inert atmosphere,2-8°C
pka: 12.87 · 12.87±0.20(Predicted)
Appearance: Brown to reddish brown Liquid
optical activity: 21 · [α]21/D 81°, c = 2 in ethanol
Water Solubility: Miscible with water, alcohol and other organic solvent. Immiscible with light petroleum.
BRN: 1280864 · 1280864
InChI: InChI=1S/C4H6O3/c5-3-1-4(6)7-2-3/h3,5H,1-2H2/t3-/m0/s1
InChIKey

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

Warning

H315 (95.7%): 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)

Hazard information

Regulatory InformationStatus: Active Update: 15-12-2008 https://echa.europa.eu/registration-dossier/-/registered-dossier/2329

Hazard Classes and Categories · 4 items

Skin Sens. 1 (100%)

Skin Irrit. 2 (95.7%)

Skin sensitisation - category 1

Skin Sens. 1

Safety data

F: 3-10
PPE: Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
hs_code: 29322090
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36-37/39
Storage Class: 10 - Combustible liquids
target organs: Respiratory system
Hazard statements: H315-H319-H335
REACH Registrations

Chemistry & industry

Applications · 2 items

Description(S)-3-Hydroxy-gamma-butyrolactone is an important intermediate in organic synthesis and an important chiral pool. It is mainly used in the synthesis of some natural products and some bioactive chiral drugs or antibiotic chiral drugs. For example, it is a key intermediate in synthesis of nerve regulator (R)-GABOB and brain metabolic accelerant S-oxiracetam (S-ORC). It can be deoxidized to (S)-(+)-3-Hydroxytetrahydrofuran which is an important intermediate of anti-AIDS drugs. It is also used in the synthesis of S(-)-3-hydroxy-4-bromobutyric acid which is a potential stabilizer.

Uses(S)-3-Hydroxy-γ-butyrolactone can be used as an anticancer drug resistance inhibitor.