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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:
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.)

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Youssef Harrak et al.
Journal of medicinal chemistry, 53(18), 6560-6571 (2010-09-02)
Following our previous research on anti-inflammatory drugs (NSAIDs), we report on the design and synthesis of 4-(aryloyl)phenyl methyl sulfones. These substances were characterized for their capacity to inhibit cyclooxygenase (COX-1 and COX-2) isoenzymes. Molecular modeling studies showed that the methylsulfone
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
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