3-HYDROXYBUTANOIC ACID, (R)-

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C4H8O3
Molecular Weight	104.1045
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 3-HYDROXYBUTANOIC ACID, (R)-

Structure Search

SMILES

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

InChI

InChIKey=WHBMMWSBFZVSSR-GSVOUGTGSA-N

InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C4H8O3
Molecular Weight	104.1045
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27528626 | https://www.google.com/patents/WO2010021766A1

(R)-3'-hydroxybutyl (R)-3'-hydroxybutyrate or D-β-hydroxybutyrate ester is a is an effective and palatable precursor to the ketone body. Ketone bodies are the most energy-efficient fuel and yield more ATP per mole of substrate than pyruvate and increase the free energy released from ATP hydrolysis. Ketone diet containing (R)-3-hydroxybutyl (R)-3-hydroxybutyrate, improved physical performance and cognitive function in rats, and its energy-sparing properties suggest that it may help to treat a range of human conditions with metabolic abnormalities. It may be used to treat a condition which is caused by, exacerbated by or associated with elevated plasma levels of free fatty acids in a human or animal subject, for instance a condition where weight loss or weight gain is implicated, or to promote alertness or improve cognitive function, or to treat, prevent or reduce the effects of, neurodegeneration, free radical toxicity, hypoxic conditions or hyperglycaemia. It has been approved by the FDA as “Generally Regarded as Safe (GRAS)”.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
energy homeostasis 2 Target ID: GO:0097009 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27528626	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Fatigue 46 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27528626 https://www.ncbi.nlm.nih.gov/pubmed/22561291	Preventing		Approved 8429	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Oral 28-day and developmental toxicity studies of (R)-3-hydroxybutyl (R)-3-hydroxybutyrate.	2012 Jul	22504461
The Population Pharmacokinetics of D-β-hydroxybutyrate Following Administration of (R)-3-Hydroxybutyl (R)-3-Hydroxybutyrate.	2016 May	26893218

Patents

Sample Use Guides

In Vivo Use Guide

(R)-3-hydroxybutyl (R)-3-hydroxybutyrate, a ketone monoester, was administered at 140, 357, and 714 mg/kg body weight, three times daily, over 5 days (equivalent to 0.42, 1.07, and 2.14 g/kg/d). The ketone ester was generally well-tolerated, although some gastrointestinal effects were reported, when large volumes of milk-based drink were consumed, at the highest ketone monoester dose. Together, these results suggest ingestion of (R)-3-hydroxybutyl (R)-3-hydroxybutyrate is a safe and simple method to elevate blood ketone levels, compared with the inconvenience of preparing and consuming a ketogenic diet.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:10:16 GMT 2023` Edited by `admin` on `Sat Dec 16 08:10:16 GMT 2023`
Record UNII	148ULJ1DF4
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

3-HYDROXYBUTANOIC ACID, (R)-

Common Name

English

D-(-)-.BETA.-HYDROXYBUTYRIC ACID

Common Name

English

(R)-3-HYDROXYBUTYRIC ACID

Systematic Name

English

BUTANOIC ACID, 3-HYDROXY-, (3R)-

Common Name

English

3-HYDROXYBUTYRIC ACID, (R)-

Common Name

English

(-)-3-HYDROXY-N-BUTYRIC ACID

Common Name

English

.BETA.-HYDROXYBUTYRIC ACID L-FORM [MI]

Common Name

English

D-(-)-3-HYDROXYBUTYRATE

Common Name

English

3-HYDROXYBUTYRIC ACID, (R)

Common Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

621755