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Details

Stereochemistry ABSOLUTE
Molecular Formula C8H16O4
Molecular Weight 176.2102
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 3'-HYDROXYBUTYL (3R)-3-HYDROXYBUTANOATE, (3'R)-

SMILES

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

InChI

InChIKey=AOWPVIWVMWUSBD-RNFRBKRXSA-N
InChI=1S/C8H16O4/c1-6(9)3-4-12-8(11)5-7(2)10/h6-7,9-10H,3-5H2,1-2H3/t6-,7-/m1/s1

HIDE SMILES / InChI
(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)”.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Kinetics, safety and tolerability of (R)-3-hydroxybutyl (R)-3-hydroxybutyrate in healthy adult subjects.
2012 Aug
Patents

Sample Use Guides

(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
Name Type Language
3'-HYDROXYBUTYL (3R)-3-HYDROXYBUTANOATE, (3'R)-
Common Name English
3(R)-HYDROXYBUTYL 3(R)-HYDROXYBUTYRATE
Systematic Name English
(R)-HYDROXYBUTYL (R)-3-HYDROXYBUTYRATE ESTER
Common Name English
D-.BETA.-HYDROXYBUTYRATE ESTER
Common Name English
KETONE ESTER
Common Name English
D-BETA-HYDROXYBUTYRATE-(R)-1,3 BUTANEDIOL MONOESTER
Common Name English
BUTANOIC ACID, 3-HYDROXY-, (3R)-3-HYDROXYBUTYL ESTER, (3R)-
Systematic Name English
(R)-HYDROXYBUTYL (R)-3-HYDROXYBUTYRATE
Common Name English
Code System Code Type Description
FDA UNII
X587FW0372
Created by admin on Sat Dec 16 09:58:08 GMT 2023 , Edited by admin on Sat Dec 16 09:58:08 GMT 2023
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EPA CompTox
DTXSID20660064
Created by admin on Sat Dec 16 09:58:08 GMT 2023 , Edited by admin on Sat Dec 16 09:58:08 GMT 2023
PRIMARY
CAS
1208313-97-6
Created by admin on Sat Dec 16 09:58:08 GMT 2023 , Edited by admin on Sat Dec 16 09:58:08 GMT 2023
PRIMARY
PUBCHEM
44631890
Created by admin on Sat Dec 16 09:58:08 GMT 2023 , Edited by admin on Sat Dec 16 09:58:08 GMT 2023
PRIMARY