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542946

Sigma-Aldrich

(S)-(+)-4-Amino-3-hydroxybutyric acid

97%

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About This Item

Empirical Formula (Hill Notation):
C4H9NO3
CAS Number:
Molecular Weight:
119.12
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22

Pricing and availability is not currently available.

Quality Level

Assay

97%

optical activity

[α]20/D +20.0°, c = 1.7 in H2O

mp

207-212 °C

functional group

amine
carboxylic acid
hydroxyl

SMILES string

NC[C@@H](O)CC(O)=O

InChI

1S/C4H9NO3/c5-2-3(6)1-4(7)8/h3,6H,1-2,5H2,(H,7,8)/t3-/m0/s1

InChI key

YQGDEPYYFWUPGO-VKHMYHEASA-N

General description

(S)-(+)-4-Amino-3-hydroxybutyric acid [(S)-GABOB] can be prepared starting from ethyl (S)-4-chloro-3-hydroxybutyrate.[1]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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    T Hata et al.
    Nihon yakurigaku zasshi. Folia pharmacologica Japonica, 91(3), 163-171 (1988-03-01)
    SART-stressed (repeated cold-stressed) rats, experimental model animals for vagotonic-type dysautonomia, have been reported to show EEG with lower-amplitude fast waves during resting-arousal and higher-amplitude slow waves during slow-wave sleep compared to normal rats. In this report, the effects of certain
    GABAergic control of anterior pituitary function in humans.
    G B Melis et al.
    Advances in biochemical psychopharmacology, 42, 219-242 (1986-01-01)
    D Jordan et al.
    Brain research, 268(1), 105-110 (1983-05-23)
    Various doses of GABA from 0.25 to 5 mumol injected into the third ventricle decrease serum TSH rapidly. The same effect was observed with GABOB (10 mumol), the hydroxylated form of GABA. The inhibitory effect of both of these drugs
    T Noto et al.
    Journal of neurochemistry, 51(2), 548-551 (1988-08-01)
    gamma-Amino-beta-[3H]hydroxybutyric acid ([3H]-GABOB) was formed in rat brain from 2-[3H]-hydroxyputrescine that had been chemically synthesized from 2-oxoputrescine and [3H]sodium borohydride. After the injection of 2-[3H]hydroxyputrescine into the lateral ventricle of a rat brain, the rat was killed and then the
    E García-Flores et al.
    Stereotactic and functional neurosurgery, 69(1-4 Pt 2), 243-246 (1997-01-01)
    Total seizure frequency was evaluated among adult patients with severe partial epilepsy refractory to medical treatment. Clinical status was assessed before, and after a synthetic analog of gamma-amino-beta-hydroxybutyric acid (GABOB) was used as add-on therapy. Twenty-five patients with temporal and

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