3-Hydroxypropionic acid

HCID 68152CAS 503-66-2
Substructure searchFind similar structures

Basic information

Standard SMILES
O=C(O)CCO
InChIKey
ALRHLSYJTWAHJZ-UHFFFAOYSA-N
Molecular formula
C3H6O3
Average molar mass
90.08 g/mol
Monoisotopic mass
90.03169405

Overview

3-hydroxypropionic acid is a 3-hydroxy monocarboxylic acid that is propionic acid in which one of the hydrogens attached to the terminal carbon is replaced by a hydroxy group. It has a role as an Escherichia coli metabolite and a human metabolite. It is an omega-hydroxy-short-chain fatty acid and a 3-hydroxy monocarboxylic acid. It is functionally related to a propionic acid. It is a conjugate acid of a 3-hydroxypropionate.

Names & identifiers

Preferred name
3-Hydroxypropionic acid
IUPAC
3-hydroxypropanoic acid
English name
3-Hydroxypropionic acid
Molecular formula
C3H6O3
Molecular weight
90.08

Names & synonyms

3-Hydroxypropionic acid503-66-23-Hydroxypropanoic acidHydracrylic acidbeta-Hydroxypropionic acidhydroxypropionic acidEthylene lactic acidbeta-Lactic acid3-HydroxypropanoateC4ZF6XLD2Xbeta-hydroxypropionateCHEBI:33404
Show more names
beta-lacticacid.beta.-Lacticacid2-deoxy-glycericaciRARECHEM AL BO 01932-deoxy-Glycericacid
DTXSID50198305RefChem:94392DTXCID40120796207-974-8Propanoic acid, 3-hydroxy-3-HYDROXY-PROPANOIC ACIDEthylenelacticacidGlyceric acid, 2-deoxy-

Database identifiers

CAS
503-66-2
PubChem CID
68152
DTXSID
DTXSID50198305
ChEMBL
CHEMBL1205969
ChEBI
CHEBI:33404
UNII
C4ZF6XLD2X
EC Number
207-974-8
Nikkaji
J6.213H

Properties

Computed structural properties

XLogP
-1
Topological polar surface area
57.5 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
2
Heavy atoms
6

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesDielectric constant
Melting Point< 25 °C
Physical DescriptionSolid

Physicochemical properties

Melting point
16.8 °C · 16.8°C (estimate)
Boiling point
212 °C · 212°C (rough estimate)
Density
1.066 g/mL · 1.066 g/mL at 25 °C
refractive index
1.4489 · 1.4489
Flash point
110 ° · >110°
storage temp.
2 · 2-8°C

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 6.7% (3 of 45) of reports.

Danger

H302 (88.9%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P330, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 45 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (88.9%)

Toxicology

Health Effects · 1 item

Chronically high levels of hydroxypropionic acid are associated with at least 5 inborn errors of metabolism including: Biotinidase deficiency, Malonic Aciduria, Methylmalonate Semialdehyde Dehydrogenase Deficiency, Methylmalonic Aciduria, Methylmalonic, Aciduria Due to Cobalamin-Related Disorders and Propionic acidemia.

Toxicity Summary · 1 item

3-hydroxypropionic acid (3HP) toxicity is mediated by 3-hydroxypropionic aldehyde (reuterin). 3HP toxicity is also proposed to be related to inhibition of the chorismate and threonine super-pathways. Generally, the toxicity mechanism of 3HP is not understood at the molecular level. (A15450)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

wgk
WGK 1
hs_code
29181990
risk_code
36/37/38-41-37/38-22
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi,Xn

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm
Metabolite PathwaysMalonic Aciduria

Uses & manufacturing

UsesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Applications · 3 items

Description3-Hydroxypropionic acid (3-HP) is considered as a potential building block either for organic synthesis or high performance polymers.It is a 3-carbon carboxylic acid, structural isomer of lactic acid, which naturally exists in some thermophilic archaea and bacteria. This organic compound has been pointed out by the US Department of Energy as a promising biomass derivate, which could potentially be used for the production of high added-value chemicals like1,3-propanediol, acrylic acid, acrylamide, and bioplastics. Being 3-HP a commercially valuable, important platform chemical, researches have been conducted about its production on commercial scale, mainly from renewable sources. The biological production of 3-HP from glycerol and glucose, both based on microbial fermentation, are among the main routes studied. More specifically, research activities have been devoted to goals such as identifying novel biochemical pathways, metabolic engineering of microbial strains for the production of 3-HP, and improvements of cultivation techniques to increase 3-HP production titers. Despite intense research efforts, there are still important bottlenecks for cost efficient, large scale biological production of 3-Hydroxypropionic Acid.

Uses3-Hydroxypropionic Acid induces gene expressions and also functions as a reagent for industrial application.

UsesA three carbon non-chiral compound, 3-Hydroxypropionic acid can be used as a building block for industrial chemicals.

Upstream & downstream products

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
成都市久鼎化学技术有限公司18584079237 · [email protected]
武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]

Additional notes

DefinitionChEBI: A 3-hydroxy monocarboxylic acid that is propionic acid in which one of the hydrogens attached to the terminal carbon is replaced by a hydroxy group.

Related reactions

37 records
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Linked notes

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