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298360

Sigma-Aldrich

(R)-(−)-3-Hydroxybutyric acid sodium salt

optical purity ee: 99% (GLC)

Synonym(s):

Sodium (R)-3-hydroxybutyrate

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About This Item

Linear Formula:
CH3CH(OH)CH2CO2Na
CAS Number:
13613-65-5
Molecular Weight:
126.09
Beilstein:
6118796
MDL number:
MFCD00077788
UNSPSC Code:
12352001
PubChem Substance ID:
24857981
NACRES:
NA.22

form

solid

Quality Level

200

optical activity

[α]22/D −14°, c = 10 in H2O

optical purity

ee: 99% (GLC)

mp

149-155 °C (lit.)

SMILES string

[Na+].C[C@@H](O)CC([O-])=O

InChI

1S/C4H8O3.Na/c1-3(5)2-4(6)7;/h3,5H,2H2,1H3,(H,6,7);/q;+1/p-1/t3-;/m1./s1

InChI key

NBPUSGBJDWCHKC-AENDTGMFSA-M

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Application

(R)-(-)-3-Hydroxybutyric acid sodium salt reacts with crown ether to form a supramolecular complex, which can catalyze the regioselective ring-opening polymerization of (S)-butyrolactone to form (R)-3-hydroxybutyrate oligomers (OHBs).

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Gokel GW
Advances in Supramolecular Chemistry, 7, 61-61 (2001)
Joel S Benjamin et al.
Proceedings of the National Academy of Sciences of the United States of America, 114(1), 125-130 (2016-12-22)
Kabuki syndrome is a Mendelian intellectual disability syndrome caused by mutations in either of two genes (KMT2D and KDM6A) involved in chromatin accessibility. We previously showed that an agent that promotes chromatin opening, the histone deacetylase inhibitor (HDACi) AR-42, ameliorates
Carmen Torres-Esquivel et al.
Frontiers in cellular neuroscience, 14, 547215-547215 (2020-11-12)
Glucose supply from blood is mandatory for brain functioning and its interruption during acute hypoglycemia or cerebral ischemia leads to brain injury. Alternative substrates to glucose such as the ketone bodies (KB), acetoacetate (AcAc), and β-hydroxybutyrate (BHB), can be used
Philip Mm Ruppert et al.
Life science alliance, 4(10) (2021-08-20)
Various forms of fasting and ketogenic diet have shown promise in (pre-)clinical studies to normalize body weight, improve metabolic health, and protect against disease. Recent studies suggest that β-hydroxybutyrate (βOHB), a fasting-characteristic ketone body, potentially acts as a signaling molecule
Christopher J Terranova et al.
Cell reports, 37(8), 110044-110044 (2021-11-25)
β-hydroxybutyrate (β-OHB) is an essential metabolic energy source during fasting and functions as a chromatin regulator by lysine β-hydroxybutyrylation (Kbhb) modification of the core histones H3 and H4. We report that Kbhb on histone H3 (H3K9bhb) is enriched at proximal
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