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27635

Sigma-Aldrich

Adipic acid

meets analytical specification of Ph.Eur., BP, E 355, 99.6-101.0% (calc. to the dried substance)

Synonym(s):

Hexanedioic acid

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About This Item

Linear Formula:
HOOC(CH2)4COOH
CAS Number:
Molecular Weight:
146.14
Beilstein:
1209788
EC Number:
MDL number:
UNSPSC Code:
12352106
eCl@ss:
39021711
PubChem Substance ID:
form:
solid
Assay:
99.6-101.0% (calc. to the dried substance)

vapor density

5 (vs air)

vapor pressure

1 mmHg ( 159.5 °C)

Assay

99.6-101.0% (calc. to the dried substance)

form

solid

autoignition temp.

788 °F

quality

meets analytical specification of Ph.Eur., BP, E 355

impurities

residual solvents, complies
≤0.001% heavy metals (as Pb)
≤0.2% water (Karl Fischer)

ign. residue

≤0.002% (as SO4)

loss

≤0.2% loss on drying, 105 °C

bp

265 °C/100 mmHg (lit.)

mp

151-154 °C (lit.)
151-154 °C

solubility

H2O: slightly soluble
H2O: soluble (Boiling)
acetone: soluble
benzene: insoluble
cyclohexane: slightly soluble
ethanol: freely soluble
methanol: freely soluble
petroleum ether: insoluble

anion traces

chloride (Cl-): ≤50 mg/kg
nitrate (NO3-): ≤30 mg/kg
sulfate (SO42-): ≤500 mg/kg

cation traces

As: ≤3 mg/kg
Fe: ≤5 mg/kg
Hg: ≤1 mg/kg
Pb: ≤10 mg/kg
Pb: ≤5 mg/kg

suitability

passes test for appearance of solution

SMILES string

OC(=O)CCCCC(O)=O

InChI

1S/C6H10O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2,(H,7,8)(H,9,10)

InChI key

WNLRTRBMVRJNCN-UHFFFAOYSA-N

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Application

Adipic acid is an organic acid used for resolving the problem of pH-dependent release of weakly basic drugs.

Biochem/physiol Actions

Presence of adipic acid in the urine of ketotic patients is utilized as a marker for diagnosing the degree of ketosis.

Preparation Note

Adipic acid is freely soluble in ethanol and methanol. It also dissolves in boiling water, and acetone. Additionally, the product is slightly soluble in water and cyclohexane and is practically insoluble in benzene and petroleum ether.

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

384.8 °F - closed cup

Flash Point(C)

196 °C - closed cup


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The occurrence of adipic and suberic acid in urine from ketotic patients.
J E Pettersen et al.
Clinica chimica acta; international journal of clinical chemistry, 38(1), 17-24 (1972-04-01)
A Streubel et al.
Journal of controlled release : official journal of the Controlled Release Society, 67(1), 101-110 (2000-04-25)
Weakly basic drugs or salts thereof demonstrate pH-dependent solubility. The resulting release from conventional matrix tablets decreases with increasing pH-milieu of the gastrointestinal tract. The aim of this study was to overcome this problem and to achieve pH-independent drug release.
J B J H van Duuren et al.
Biotechnology and bioengineering, 108(6), 1298-1306 (2011-02-18)
A limited life cycle assessment (LCA) was performed on a combined biological and chemical process for the production of adipic acid, which was compared to the traditional petrochemical process. The LCA comprises the biological conversion of the aromatic feedstocks benzoic
J Greter et al.
The Journal of biological chemistry, 254(8), 2807-2813 (1979-04-25)
cis-3,4-Methylene hexanedioic acid has been discovered in human urine. It has been isolated and identified by mass spectrometry and synthesis. The daily excretion in nine subjects on a free diet was 88 mumol/day (range, 32 to 144 mumol/day). cis-3,4-Methylene hexanedioic
Holger Noack et al.
Inorganic chemistry, 50(4), 1194-1202 (2011-01-28)
Adipic acid is a key compound in the chemical industry, where it is mainly used in the production of polymers. The conventional process of its generation requires vast amounts of energy and, moreover, produces environmentally deleterious substances. Thus, there is

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