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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:
124-04-9
Molecular Weight:
146.14
Beilstein:
1209788
EC Number:
204-673-3
MDL number:
MFCD00004420
UNSPSC Code:
12352106
eCl@ss:
39021711
PubChem Substance ID:
329753005

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
GHS05

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338

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

Regulatory Information

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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.
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)
Roohan Rakhshaee et al.
Journal of hazardous materials, 189(1-2), 158-166 (2011-03-15)
The removal of methylene blue (MB) as a cationic dye from aqueous solution by the stabilized Fe(3)O(4) nano-particles with the extracted pectin from apple waste (FN-PA) increased due to using the cross-linked forms of the bound pectin on the nano-particles
H V Pawar et al.
Colloids and surfaces. B, Biointerfaces, 102, 102-110 (2012-09-26)
Streptomycin (STP) and diclofenac (DLF) loaded film dressings were prepared by blending Polyox(®) (POL) with four hydrophilic polymers [hydroxypropylmethylcellulose (HPMC), carrageenan (CAR), sodium alginate (SA) or chitosan (CS)] using glycerol (GLY) as plasticiser. The films were characterised by scanning electron
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
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