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I106

Sigma-Aldrich

(S)-(+)-Ibuprofen

solid

Synonym(s):

(S)-(+)-2-(4-Isobutylphenyl)propionic acid, (S)-(+)-4-Isobutyl-α-methylphenylacetic acid

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About This Item

Linear Formula:
(CH3)2CHCH2C6H4CH(CH3)CO2H
CAS Number:
51146-56-6
Molecular Weight:
206.28
Beilstein/REAXYS Number:
3590022
MDL number:
MFCD00069289
UNSPSC Code:
12352000
PubChem Substance ID:
24278501

form

solid

optical activity

[α]26/D +54.46°, c = 0.6 in methanol(lit.)

color

white

mp

49-53 °C (lit.)

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1.5 mg/mL
0.1 M NaOH: insoluble
methanol: soluble

SMILES string

CC(C)Cc1ccc(cc1)[C@H](C)C(O)=O

InChI

1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)/t10-/m0/s1

InChI key

HEFNNWSXXWATRW-JTQLQIEISA-N

Gene Information

human ... IL8RA(3577)

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Biochem/physiol Actions

Anti-inflammatory and analgesic. Active isomer of ibuprofen.

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
048H4638

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2-Propanol anhydrous, 99.5%

Sigma-Aldrich

278475

2-Propanol

P Jeffrey et al.
The Journal of pharmacy and pharmacology, 43(10), 715-720 (1991-10-01)
The site of metabolic inversion of R(-)-ibuprofen to the pharmacologically active S(+)-enantiomer has been investigated using an array of in-situ rat perfused organ preparations allowing vascular perfusion (55-60 min) of the separate or combined intestine and liver. After addition of
R Mehvar et al.
Clinical chemistry, 34(3), 493-496 (1988-03-01)
This stereospecific "high-performance" liquid-chromatographic (HPLC) assay is suitable for pharmacokinetic studies of ibuprofen (IB). Very efficient extraction of the drug and internal standard, (+/-)-2-(4-benzoylphenyl)butyric acid, from plasma with isooctane/isopropanol (95/5, by vol) is followed by sequential reaction of the enantiomers
R Mehvar et al.
Pharmaceutical research, 5(2), 76-79 (1988-02-01)
Equations describing plasma concentration-time courses of the individual enantiomers of chiral 2-arylpropionic acid nonsteroidal antiinflammatory drugs were derived from a general model. The model assumes first-order absorption and elimination of the enantiomers with presystemic and/or systemic R-to-S enantiomeric inversion. Utilizing
Surjeet Singh et al.
Bioorganic & medicinal chemistry letters, 17(13), 3706-3711 (2007-05-08)
The present study revealed the synergistic effect of boswellic acid mixture (BA) and glucosamine for anti-inflammatory and anti-arthritic activities in rats. Two studies were conducted, that is, acute anti-inflammatory by carrageenan edema and chronic anti-arthritic by Mycobacterium-induced developing arthritis. Five
Hong Su et al.
Bioorganic & medicinal chemistry letters, 21(12), 3578-3582 (2011-05-24)
Newly developed monofluoromethylation reaction provided access to various bioactive molecules with an interesting monofluoromethyl unit. An iridium-catalyzed asymmetric version was employed for large-scale methyl-monofluorination of widely used nonsteroidal anti-inflammatory drug ibuprofen (the active S isoform). The methyl-monofluorinated ibuprofen was found
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