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375160

Sigma-Aldrich

(S)-(+)-Ibuprofen

ReagentPlus®, 99%

Synonym(s):

S-(+)-IBU, (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:
12352002
PubChem Substance ID:
24863369
NACRES:
NA.22

product line

ReagentPlus®

assay

99%

form

powder

optical activity

[α]20/D +59°, c = 2 in ethanol

mp

49-53 °C (lit.)

functional group

carboxylic acid

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) , PTGS1(5742) , PTGS2(5743)

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General description

(S)-(+)-Ibuprofen is the enantiomer associated with the anti-inflammatory action of ibuprofen, which is widely used as a nonsteroidal anti-inflammatory drug in racemic form.

Application

(S)-(+)-Ibuprofen may be used as a starting material to synthesize hydrogelators with the potential ability to release it via enzyme-mediated hydrolysis.
Enantiomeric form of the anti-inflammatory agent ibuprofen used in pharmacokinetic studies.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - 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
BCCD7027
BCCD5855
BCBT9452
BCBR3849V
BCBQ0296V

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F Jamali et al.
Journal of pharmaceutical sciences, 81(3), 221-225 (1992-03-01)
The influences of absorption rate and dosage size on the pharmacokinetics of ibuprofen (IB) enantiomers were studied in six healthy subjects. Rapidly absorbed solutions (50, 100, 200, 400, 600, and 1200 mg) and regular 600-mg tablets of racemic IB were
(S)-(+)-Ibuprofen-based hydrogelators: an approach toward anti-inflammatory drug delivery.
Bhuniya S, et al.
Tetrahedron Letters, 47(40), 7153-7156 (2006)
Enantioselective determination of ibuprofen in plasma by high-performance liquid chromatography-electrospray mass spectrometry.
Bonato PS, et al.
Journal of Chromatography. B, Biomedical Sciences and Applications, 796(2), 413-420 (2003)
Jennifer Manley et al.
The Annals of pharmacotherapy, 41(7), 1227-1232 (2007-05-24)
To evaluate the literature examining prophylactic use of acetaminophen and ibuprofen for prevention of adverse reactions associated with childhood immunization. Articles were identified via MEDLINE/PubMed/EMBASE (1966-March 2007) using the following key terms: vaccination, immunization, diphtheria-tetanus toxoids-whole pertussis (DTwP), diphtheria tetanus-toxoid
Elizabeth R Southey et al.
Current medical research and opinion, 25(9), 2207-2222 (2009-07-18)
The main aim of this review was to compare the tolerability and safety between ibuprofen and paracetamol when used as anti-pyretic and analgesic agents in children up to 18 years of age. MEDLINE (1950 to November 2008), EMBASE (1980 to
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