CAS 26063-00-3 3-Hydroxybutyric Acid (HCID 441)

Overview

3-hydroxybutyric acid is a straight-chain 3-hydroxy monocarboxylic acid comprising a butyric acid core with a single hydroxy substituent in the 3- position; a ketone body whose levels are raised during ketosis, used as an energy source by the brain during fasting in humans. Also used to synthesise biodegradable plastics. It has a role as a human metabolite. It is a hydroxybutyric acid, a 3-hydroxy monocarboxylic acid and an (omega-1)-hydroxy fatty acid. It is functionally related to a butyric acid. It is a conjugate acid of a 3-hydroxybutyrate.

Names & identifiers

Preferred name: 3-Hydroxybutyric Acid
IUPAC: 3-hydroxybutanoic acid
English name: POLY(3-HYDROXYBUTYRIC ACID)
Molecular formula: C12H18O6X2
Molecular weight: 104.1

Names & synonyms

3-hydroxybutyric acid3-hydroxybutanoic acid300-85-6Butanoic acid, 3-hydroxy-beta-Hydroxybutyric acid3 HBA3-Hydroxybuttersaeurebeta-HydroxybuttersaeureDL-beta-Hydroxybutyric acidbeta-Hydroxy-n-butyric acid3-hydroxy-butanoic acidbeta-hydroxy-butyrate

Show more names

POLY(3-HYDROXYBUTYRATE)Poly(a-hydroxybutyrate)poly-beta-hydroxybutyratePoly(3-hydroxyvalericacid)Poly-β-Hydroxybutyric AcidPOLY(3-HYDROXYBUTYRIC ACID)Poly[(R)-3-hydroxybutyrate]Poly-beta-hydroxybutyric acidPOLY[(-)3-HYDROXYBUTYRIC ACID]POLY(3-HYDROXYBUTYRATE) OLIGOMER

(1)-3-Hydroxybutyric acidHydroxybutyric acid, dl-NSC-3806TZP1275679CHEBI:20067DTXSID608595113 Hydroxybutyric Acidbeta Hydroxybutyric Acid

Database identifiers

CAS: 26063-00-3、300-85-6、625-71-8
PubChem CID: 441
DTXSID: DTXSID60859511
ChEMBL: CHEMBL1162496
ChEBI: CHEBI:20067
UNII: TZP1275679
EC Number: 206-099-9、210-908-0
Nikkaji: J4.451B、J507J

Properties

Computed structural properties

XLogP: -0.5
Topological polar surface area: 57.5 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 3
Rotatable bonds: 2
Heavy atoms: 7
Formal charge: 0
Complexity: 69.3

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Organic Acids

LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Hydroxy fatty acids [FA0105]

SpringerMaterials PropertiesChemical shift

Food Contact SubstancesFCS -> FDA Cumulative Estimated Daily Intake (CEDI)

Physical DescriptionHygroscopic liquid; [Merck Index] Clear, colorless to light yellow viscous liquid; Hygroscopic; [Acros Organics MSDS]

Collision Cross Section · 2 items

137.54 Å² [M-H]- [CCS Type: DT; Method: stepped-field]

137.1 Å² [M-H]-

Physicochemical properties

Melting point: 47 · 47-180 °C
Density: 1.2 g/cm3 · 1.2 g/cm3
storage temp.: 2 · 2-8°C
form: powder
color: white to off-white
UNSPSC Code: 12352106 · 12352106
NACRES: 25 · NA.25
WGK Germany: 3 · 3
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 44 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

Hazard information

Regulatory Information · 2 items

Chemical: Butanoic acid, 3-hydroxy-

3-Hydroxybutyric acid: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment

Hazards SummaryAn irritant; [Acros Organics MSDS] See Butyric acid.

Hazard Classes and Categories · 2 items

Skin Irrit. 2 (100%)

Safety data

wgk: 3
Storage Class: 11 - Combustible Solids

Chemistry & industry

Pharmacology

Mechanism of Action · 1 item

Beta-hydroxybutyrate is a small molecule endogenous ketone body and metabolite synthesized in the liver from fatty acids. It is an energy carrier that moves energy from the liver to the peripheral tissues in times when glucose supply is too low for the energetic needs of the body. This ketone body has also been seen to have cellular signaling functions that link the outside environment to cellular function and epigenetic gene regulation. Beta-hydroxybutyrate has potential applications in a variety of diseases and human aging and is currently being investigated against COVID-19.

Uses & manufacturing

UsesKetone produced in the liver; [ChemIDplus]

General Manufacturing InformationButanoic acid, 3-hydroxy-: ACTIVE

Applications · 1 item

UsesPoly(3-hydroxybutyric acid) (PHB) is a common polyhydroxyalkanoate (PHA), it has been widely used for food packaging, medical implants, biodegradable sutures and drug delivery systems due to its biocompatible and biodegradable properties. PHB has been investigated as drug delivery micro- and nano-carriers.