Page last updated: 2024-12-06

beta-hydroxyisovaleric acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

3-hydroxyisovaleric acid : A 3-hydroxy monocarboxylic acid that is isovaleric acid substituted at position 3 by a hydroxy group. Used as indicator of biotin deficiency. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID69362
CHEMBL ID4303793
CHEBI ID37084
SCHEMBL ID95499
MeSH IDM0046207

Synonyms (60)

Synonym
3-methyl-3-hydroxybutyric acid
625-08-1
beta-hydroxy-beta-methylbutyric acid
3-hydroxy-3-methylbutyric acid ,
CHEBI:37084
3-hydroxyisovaleric acid
hmb-d6
beta-hydroxyisovaleric acid
3-hydroxy-isovaleric acid
3-oh-isovaleric acid
3-hydroxy-3-methylbutanoic acid
beta-hydroxyisovaleric acid, >=95.0% (t)
FT-0692252
H0701
LMFA01050396
3-hydroxy-3-methyl-butanoic acid
A833816
AKOS005254540
beta-(hydroxyisovaleric acid)
unii-3f752311cd
beta-hydroxy-beta-methylbutyrate
3f752311cd ,
beta-hydroxy-methylbutyrate
beta-hydroxy beta-methylbutyric acid
S6124
SCHEMBL95499
hydroxy-beta-methylbutyrate [vandf]
butanoic acid, 3-hydroxy-3-methyl-
.beta.-hydroxy-.beta.-methylbutyrate
juven
.beta.-hydroxyisovaleric acid
butyric acid, 3-hydroxy-3-methyl-
juven [vandf]
beta-hydroxy-beta-methylbutyrate [who-dd]
3-hydroxy-3-methyl-butanoate
3-hydroxy-3-methyl butyric acid
b-hydroxyisovaleric acid
3-hydroxy-3-methyl-butyric acid
C20827
.beta.-hydroxy-isovaleric acid
mfcd00059081
DTXSID20211535
b-hydroxy-b-methylbutyrate
b-hydroxyisovalerate
b-hydroxy-b-methylbutyric acid
CS-0059394
HY-113409
123743-99-7
STL554349
DS-9861
SY032937
DB15344
Q223081
beta-hydroxyisovaleric acid-d8
BBL100555
CHEMBL4303793
EN300-117931
?beta-hydroxyisovaleric acid
beta -hydroxyisovaleric acid
Z982131798

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" There were no CaHMB-related adverse effects on clinical observations, body weights, food consumption, clinical chemistry, hematology, absolute or relative organ weights, or macroscopic or microscopic observations."( Dietary toxicity of calcium beta-hydroxy-beta-methyl butyrate (CaHMB).
Baxter, JH; Bultman, J; Carlos, JL; Frost, D; Rehani, RN; Thurmond, J, 2005
)
0.33
" Studies in humans and animals provide evidence that there are no adverse effects associated with HMB supplementation."( [β-hydroxy-β-methylbutyrate as a dietary supplement (I): metabolism and toxicity].
Alvear-Ordenes, I; González-Gallego, J; Manjarrez-Montes-de-Oca, R; Torres-Vaca, M, 2014
)
0.4

Pharmacokinetics

ExcerptReferenceRelevance
" There was no significant sex by treatment interaction for any of the pharmacokinetic parameters measured."( Comparison of availability and plasma clearance rates of β-hydroxy-β-methylbutyrate delivery in the free acid and calcium salt forms.
Angus, HF; Fuller, JC; Khoo, PY; Rathmacher, JA; Sharp, RL, 2015
)
0.42

Compound-Compound Interactions

ExcerptReferenceRelevance
" AFM nanoindentation measurements collected from animals administered with HMB displayed an increase in AC tissue stiffness by detecting a higher value of Young's modulus in all investigated AC zones."( Fourier Transform Infrared Microspectroscopy Combined with Principal Component Analysis and Artificial Neural Networks for the Study of the Effect of β-Hydroxy-β-Methylbutyrate (HMB) Supplementation on Articular Cartilage.
Arciszewski, MB; Arczewska, M; Aszodi, A; Blicharski, T; Clausen-Schaumann, H; Dobrowolski, P; Gagoś, M; Kras, K; Muszyński, S; Prein, C; Świetlicka, I; Świetlicki, M; Tomaszewska, E, 2021
)
0.62

Bioavailability

ExcerptReferenceRelevance
" The developed assay method was applied to a bioavailability study in rats."( Development and validation of LC-MS/MS method for the estimation of β-hydroxy-β-methylbutyrate in rat plasma and its application to pharmacokinetic studies.
Chunduri, RH; Das, T; Deshpande, P; Jie, Z; Mamidi, VK; Shreeram, S; Subbarayan, R, 2013
)
0.39
"The present study was designed to compare the pharmacokinetics and relative bioavailability of the 2 forms of HMB administered as a liquid suspension in male Sprague-Dawley rats."( The relative bioavailability of the calcium salt of β-hydroxy-β-methylbutyrate is greater than that of the free fatty acid form in rats.
Gelling, RW; Johns, PW; Mamidi, VK; Mandal, S; Puthan, JK; Ramesh, S; Shreeram, S; Subramaniam, S; Vaidyanathan, V, 2014
)
0.4
" Plasma concentrations of HMB were analyzed by liquid chromatography tandem mass spectrometry, and pharmacokinetic variables and relative bioavailability of the 2 forms of HMB were determined."( The relative bioavailability of the calcium salt of β-hydroxy-β-methylbutyrate is greater than that of the free fatty acid form in rats.
Gelling, RW; Johns, PW; Mamidi, VK; Mandal, S; Puthan, JK; Ramesh, S; Shreeram, S; Subramaniam, S; Vaidyanathan, V, 2014
)
0.4
" The relative bioavailability of CaHMB was 49%, 54%, and 27% greater than that of FAHMB for the 3 respective oral doses tested."( The relative bioavailability of the calcium salt of β-hydroxy-β-methylbutyrate is greater than that of the free fatty acid form in rats.
Gelling, RW; Johns, PW; Mamidi, VK; Mandal, S; Puthan, JK; Ramesh, S; Shreeram, S; Subramaniam, S; Vaidyanathan, V, 2014
)
0.4
"This study demonstrates the enhanced relative bioavailability of CaHMB compared with FAHMB."( The relative bioavailability of the calcium salt of β-hydroxy-β-methylbutyrate is greater than that of the free fatty acid form in rats.
Gelling, RW; Johns, PW; Mamidi, VK; Mandal, S; Puthan, JK; Ramesh, S; Shreeram, S; Subramaniam, S; Vaidyanathan, V, 2014
)
0.4
" The current study was conducted to compare the bioavailability of HMB using the two commercially available capsule forms of HMB-FA and Ca-HMB."( Comparison of availability and plasma clearance rates of β-hydroxy-β-methylbutyrate delivery in the free acid and calcium salt forms.
Angus, HF; Fuller, JC; Khoo, PY; Rathmacher, JA; Sharp, RL, 2015
)
0.42
" Of the two available forms of HMB (calcium (Ca-HMB) salt or free acid (FA-HMB)) - differences in plasma bioavailability have been reported."( Impact of the calcium form of β-hydroxy-β-methylbutyrate upon human skeletal muscle protein metabolism.
Ashcroft, S; Atherton, PJ; Brook, MS; Cegielski, J; Hossain, T; Limb, MC; Lund, J; Phillips, BE; Philp, A; Rathmacher, JA; Smith, K; Szewczyk, NJ; Wilkinson, DJ; Williams, JP, 2018
)
0.48

Dosage Studied

ExcerptRelevanceReference
"Biotin deficiency associated with total parenteral nutrition is an emerging clinical problem; criteria for diagnosis and dosage for treatment are unclear."( Biotin deficiency complicating parenteral alimentation: diagnosis, metabolic repercussions, and treatment.
Baker, H; Baswell, DL; Holman, RT; Mock, DM; Sweetman, L, 1985
)
0.27
" In conclusion, young growing rats were sensitive to the dosage of dexamethasone, but in contrast to lymphoid tissue, could easily compensate the outcomes of impaired antioxidative defence within 5 days of recovery."( Excess of glucocorticoids impairs whole-body antioxidant status in young rats. relation to the effect of dexamethasone in soleus muscle and spleen.
Balasińska, B; Brodnicka, A; Grzelkowska, K; Jank, M; Mrówczyńska, A; Olczak, J; Orzechowski, A; Ostaszewski, P; Ploszaj, T; Wilczak, J, 2000
)
0.31
" These are described here, and hormonal interactions are discussed, along with HMB dosage and safety issues."( Effect of HMB supplementation on body composition, fitness, hormonal profile and muscle damage indices.
Eliakim, A; Halevy, O; Nemet, D; Portal, S; Zadik, Z, 2010
)
0.36
" Dose-response curves for FAO were constructed and the highest non-effective dose (typically 1-10 nM) was used with either leucine (0."( Synergistic effects of polyphenols and methylxanthines with Leucine on AMPK/Sirtuin-mediated metabolism in muscle cells and adipocytes.
Bruckbauer, A; Zemel, MB, 2014
)
0.4
" The equivalent human dosage using body surface area conversion would be 402 and 459 mg/kg BW d(-1) for men and women, respectively."( Subchronic toxicity study of β-hydroxy-β-methylbutyric free acid in Sprague-Dawley rats.
Arp, LH; Baier, SM; Diehl, LM; Fuller, JC; Landin, KL; Rathmacher, JA, 2014
)
0.4
" Quality of life (EORTC QLQ-C30/PROMS) at baseline and upon radiotherapy at a dosage of 50 Gy were assessed."( A phase II study of HMB/Arg/Gln against oral mucositis induced by chemoradiotherapy for patients with head and neck cancer.
Hamauchi, S; Mori, K; Ogawa, H; Onitsuka, T; Onoe, T; Suzuki, M; Yamashita, A; Yokota, T; Yoshida, Y; Yurikusa, T, 2018
)
0.48
" Sorafenib dosage was 400 mg/day for both groups."( β-Hydroxy-β-methyl Butyrate/L-Arginine/L-Glutamine Supplementation for Preventing Hand-Foot Skin Reaction in Sorafenib for Advanced Hepatocellular Carcinoma.
Hatanaka, T; Horiguchi, S; Hoshino, T; Ishihara, H; Kakizaki, S; Kudo, T; Murakami, T; Naganuma, A; Ogawa, Y; Ohno, N; Sato, K; Suzuki, Y; Takagi, H; Uehara, D,
)
0.13
" Moreover, HMB seems to be more potent than Leu in the positive regulation of mitochondrial biogenesis and function in C2 C12 myotubes because the dosage used for HMB was much lower than that for Leu."( β-hydroxy-β-methylbutyrate (HMB) improves mitochondrial function in myocytes through pathways involving PPARβ/δ and CDK4.
Deng, J; Duan, Y; Li, F; Zeng, L; Zhong, Y, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
3-hydroxy monocarboxylic acidA hydroxy monocarboxylic acid that has a hydroxy group beta to the carboxy group.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (426)

TimeframeStudies, This Drug (%)All Drugs %
pre-199028 (6.57)18.7374
1990's31 (7.28)18.2507
2000's84 (19.72)29.6817
2010's210 (49.30)24.3611
2020's73 (17.14)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 18.03

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index18.03 (24.57)
Research Supply Index6.36 (2.92)
Research Growth Index5.09 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (18.03)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials134 (30.32%)5.53%
Reviews63 (14.25%)6.00%
Case Studies37 (8.37%)4.05%
Observational0 (0.00%)0.25%
Other208 (47.06%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]