CAS 18069-17-5 2-Methylglutaric Acid (HCID 12046)

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Basic information

CAS: 18069-17-5
Standard SMILES: CC(CCC(=O)O)C(=O)O
InChIKey: AQYCMVICBNBXNA-UHFFFAOYSA-N
Molecular formula: C6H10O4
Average molar mass: 146.14 g/mol
Monoisotopic mass: 146.0579088

Overview

2-methylglutaric acid is an alpha,-dicarboxylic acid that is glutaric acid substituted at position 2 by a methyl group. It has a role as a mammalian metabolite. It is a dicarboxylic fatty acid and an alpha,omega-dicarboxylic acid. It is functionally related to a glutaric acid. It is a conjugate acid of a 2-methylglutarate(2-).

Names & identifiers

Preferred name: 2-Methylglutaric Acid
IUPAC: 2-methylpentanedioic acid
English name: 2-Methylglutaric acid
Molecular formula: C6H10O4
Molecular weight: 146.14

Names & synonyms

2-METHYLGLUTARIC ACID18069-17-5CHEBI:68567RefChem:476053620-991-92-Methylpentanedioic acid617-62-9alpha-Methylglutaric acidPentanedioic acid, 2-methyl-Glutaric acid, 2-methyl-2-METHYLGLUTARICACID2-Methylglutarate

Show more names

AKOS 237-134RARECHEM AL BO 0092A-METHYLGLUTARIC ACID2-MethylglutaricAcid98%2-Methylglutaric acid 98%2-Methylglutaric acid,99%2-Methylglutaric Acid (Solution)Pentanedioic acid, 2-methyl-, (.+/-.)-

.alpha.-Methylglutaric acid2-methyl-glutaric acidNSC408456Pentanedioic acid,2-methyl-DTXSID4021632MFCD000026612-methyl-pentanedioic acid2-Methylglutaric acid, 98%

Database identifiers

CAS: 18069-17-5、617-62-9
PubChem CID: 12046
DTXSID: DTXSID4021632
ChEMBL

Properties

Computed structural properties

XLogP: 0.1
Topological polar surface area: 74.6 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 4
Rotatable bonds: 4
Heavy atoms: 10
Formal charge: 0
Complexity: 141

Experimental & physicochemical properties

LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Dicarboxylic acids [FA0117]

Solubility908 mg/mL

Physical DescriptionSolid

Collision Cross Section · 3 items

123.84 Å² [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

137.4 Å² [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

137.2 Å² [M+Na]+

Physicochemical properties

Melting point: 80 · 80-82 °C(lit.)
Boiling point: 214 · 214-215 °C22 mm Hg(lit.)
Density: 1.4528 · 1.4528 (rough estimate)
refractive index: 1.4336 · 1.4336 (estimate)
Flash point: 214 · 214-215°C/22mm
form: powder
BRN: 1723219 · 1723219

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H315 (90.9%): 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.

Danger

H302 (85.7%): Harmful if swallowed [Warning Acute toxicity, oral]

Hazard information

Regulatory Information · 2 items

PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.

Status: Active Update: 22-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/11216

Hazard Classes and Categories · 2 items

Acute Tox. 4 (85.7%)

Skin Irrit. 2 (90.9%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
hs_code: 29171990
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H315-H319-H335
Hazard Classifications

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

General Manufacturing InformationPentanedioic acid, 2-methyl-: ACTIVE

Applications

Uses2-Methylglutaric acid was used in the preparation of acetic acid.

Preparation methods · 1 item

PreparationStep 1: 80g diethyl malonate + 50mL DMF + 14g KF/Al2O3, oil bath 80℃, 50g methyl methacrylate dissolved in 50mL DMF was added dropwise, reaction for 5 hours. After the reaction, GC-MS analysis showed that most of the diethyl malonate was converted, and the chromatographic integral area percentage of the main intermediate was 56%. The solvents DMF and methanol were removed by vacuum distillation, and approximately 70g of product 1 was obtained by vacuum distillation at 160℃. Step 2: 0.1mol of product 1 was hydrolyzed with 0.4mol NaOH at 20℃ for 3 hours, then acidified with 0.4mol sulfuric acid, refluxed at 100℃ for decarboxylation for 4 hours, cooled, separated, and the aqueous phase was extracted with ethyl acetate 5 times. The organic phases were combined, the solvent was removed by vacuum, and GC-MS analysis showed that it was 2-methylglutaric acid (product 2). The chromatographic integral area percentage was 68%, and the yield was 60%.