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
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
| Molecular Formula | C8H16O4 |
| Molecular Weight | 176.2102 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
(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
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.28 mM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22561291/ |
140 mg/kg single, oral dose: 140 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
(R)-3-HYDROXYBUTYRIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1 mM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22561291/ |
357 mg/kg single, oral dose: 357 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
(R)-3-HYDROXYBUTYRIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
3.3 mM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22561291/ |
714 mg/kg single, oral dose: 714 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
(R)-3-HYDROXYBUTYRIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1.19 mM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22561291/ |
714 mg/kg single, oral dose: 714 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
[NO STEREO] ACETOACETIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
0.54 mM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22561291/ |
357 mg/kg single, oral dose: 357 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
[NO STEREO] ACETOACETIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
0.23 mM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22561291/ |
140 mg/kg single, oral dose: 140 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
[NO STEREO] ACETOACETIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.09 mM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22561291/ |
140 mg/kg single, oral dose: 140 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
(R)-3-HYDROXYBUTYRIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
4 mM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22561291/ |
357 mg/kg single, oral dose: 357 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
(R)-3-HYDROXYBUTYRIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
13 mM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22561291/ |
714 mg/kg single, oral dose: 714 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
(R)-3-HYDROXYBUTYRIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
7.8 mM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22561291/ |
714 mg/kg single, oral dose: 714 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
[NO STEREO] ACETOACETIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
4.19 mM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22561291/ |
357 mg/kg single, oral dose: 357 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
[NO STEREO] ACETOACETIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
2.06 mM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22561291/ |
140 mg/kg single, oral dose: 140 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
[NO STEREO] ACETOACETIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.61 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22561291/ |
140 mg/kg single, oral dose: 140 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
(R)-3-HYDROXYBUTYRIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
3.06 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22561291/ |
357 mg/kg single, oral dose: 357 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
(R)-3-HYDROXYBUTYRIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
0.77 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22561291/ |
714 mg/kg single, oral dose: 714 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
(R)-3-HYDROXYBUTYRIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
10.47 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22561291/ |
714 mg/kg single, oral dose: 714 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
[NO STEREO] ACETOACETIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
8.23 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22561291/ |
357 mg/kg single, oral dose: 357 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
[NO STEREO] ACETOACETIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
14.29 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22561291/ |
140 mg/kg single, oral dose: 140 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
[NO STEREO] ACETOACETIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
714 mg/kg 3 times / day multiple, oral Highest studied dose Dose: 714 mg/kg, 3 times / day Route: oral Route: multiple Dose: 714 mg/kg, 3 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: FED Sources: |
Disc. AE: Vomiting, Nausea... AEs leading to discontinuation/dose reduction: Vomiting (grade 3, 8.3%) Sources: Nausea (8.3%) Diarrhea (8.3%) Chest pain (8.3%) Abdominal distension (8.3%) Upper abdominal pain (8.3%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Abdominal distension | 8.3% Disc. AE |
714 mg/kg 3 times / day multiple, oral Highest studied dose Dose: 714 mg/kg, 3 times / day Route: oral Route: multiple Dose: 714 mg/kg, 3 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: FED Sources: |
| Chest pain | 8.3% Disc. AE |
714 mg/kg 3 times / day multiple, oral Highest studied dose Dose: 714 mg/kg, 3 times / day Route: oral Route: multiple Dose: 714 mg/kg, 3 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: FED Sources: |
| Diarrhea | 8.3% Disc. AE |
714 mg/kg 3 times / day multiple, oral Highest studied dose Dose: 714 mg/kg, 3 times / day Route: oral Route: multiple Dose: 714 mg/kg, 3 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: FED Sources: |
| Nausea | 8.3% Disc. AE |
714 mg/kg 3 times / day multiple, oral Highest studied dose Dose: 714 mg/kg, 3 times / day Route: oral Route: multiple Dose: 714 mg/kg, 3 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: FED Sources: |
| Upper abdominal pain | 8.3% Disc. AE |
714 mg/kg 3 times / day multiple, oral Highest studied dose Dose: 714 mg/kg, 3 times / day Route: oral Route: multiple Dose: 714 mg/kg, 3 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: FED Sources: |
| Vomiting | grade 3, 8.3% Disc. AE |
714 mg/kg 3 times / day multiple, oral Highest studied dose Dose: 714 mg/kg, 3 times / day Route: oral Route: multiple Dose: 714 mg/kg, 3 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: FED Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Novel ketone diet enhances physical and cognitive performance. | 2016-12 |
|
| The Population Pharmacokinetics of D-β-hydroxybutyrate Following Administration of (R)-3-Hydroxybutyl (R)-3-Hydroxybutyrate. | 2016-05 |
|
| An Ester of β-Hydroxybutyrate Regulates Cholesterol Biosynthesis in Rats and a Cholesterol Biomarker in Humans. | 2015-12 |
|
| Kinetics, safety and tolerability of (R)-3-hydroxybutyl (R)-3-hydroxybutyrate in healthy adult subjects. | 2012-08 |
|
| Oral 28-day and developmental toxicity studies of (R)-3-hydroxybutyl (R)-3-hydroxybutyrate. | 2012-07 |
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
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
X587FW0372
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| Record Status |
Validated (UNII)
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| Record Version |
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