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Merck

S5375

Shikimic acid

≥99%, suitable for ligand binding assays

Synonim(y):

(3R,4S,5R)-(−)-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid

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Wybierz wielkość

10 MG

203,00 zł

1 G

1240,00 zł

5 G

4950,00 zł

203,00 zł


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Informacje o tej pozycji

Wzór empiryczny (zapis Hilla):
C7H10O5
Numer CAS:
Masa cząsteczkowa:
174.15
NACRES:
NA.25
PubChem Substance ID:
UNSPSC Code:
12352106
EC Number:
205-334-2
MDL number:
Beilstein/REAXYS Number:
2210055

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Nazwa produktu

Shikimic acid, ≥99%

InChI

1S/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s1

InChI key

JXOHGGNKMLTUBP-HSUXUTPPSA-N

SMILES string

O[C@@H]1CC(=C[C@@H](O)[C@H]1O)C(O)=O

assay

≥99%

form

powder

technique(s)

ligand binding assay: suitable

color

white to off-white

mp

185-187 °C (lit.)

Quality Level

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Ta pozycja
G176369686D1156
form

powder

form

powder

form

-

form

powder

technique(s)

ligand binding assay: suitable

technique(s)

ligand binding assay: suitable

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

technique(s)

ligand binding assay: suitable

assay

≥99%

assay

≥98% (TLC)

assay

98.0-102.0% (T)

assay

≥99%

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

200

color

white to off-white

color

white to off-white

color

-

color

white to off-white

mp

185-187 °C (lit.)

mp

-

mp

185-187 °C (lit.)

mp

178-182 °C (lit.)

Application

Shikimic acid has been used as a standard for the quantification of shikimate in apical parts of roots.[1] It has also been used as a substrate in shikimate kinase assay.[2]

Biochem/physiol Actions

Shikimic acid is observed to be carcinogenic in rat models, when administered.[3] It serves as a precursor for the biosynthesis of aromatic amino acids, alkaloids and other aromatic metabolites in microorganisms.[4] Shikimic acid is known to inhibit adenosine diphosphate (ADP) induced platelet aggregation and blood coagulation in rabbits.[5]
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pictograms

Corrosion

signalword

Danger

hcodes

Hazard Classifications

Eye Dam. 1

Klasa składowania

11 - Combustible Solids

wgk

WGK 3

ppe

Eyeshields, Gloves, type N95 (US)


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Certyfikaty analizy (CoA)

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Masz już ten produkt?

Dokumenty związane z niedawno zakupionymi produktami zostały zamieszczone w Bibliotece dokumentów.

Odwiedź Bibliotekę dokumentów

Efficient elimination of nonstoichiometric enzyme inhibitors from HTS hit lists.
Habig M
Journal of Biomolecular Screening, 14(6), 679-689 (2009)
Inhibitory effects of shikimic acid on platelet aggragation and blood coagulation.
Ma Yi
Acta Pharmaceutica Sinica. B, 35, 1-3 (2000)
Amalia M Estévez et al.
Mini reviews in medicinal chemistry, 12(14), 1443-1454 (2012-07-26)
Shikimic acid, a natural compound is a key intermediate in the biosynthesis of amino acids. Consequently, this derivative is widely present in many plants and has interesting biological properties. But besides the pharmacological relevance of shikimic acid itself, it is
Varun Rawat et al.
Organic & biomolecular chemistry, 10(20), 3988-3990 (2012-04-24)
A new enantioselective synthesis of the anti-influenza agent (-)-oseltamivir free base (7.1% overall yield; 98% ee) and (-)-methyl 3-epi-shikimate (16% overall yield; 98% ee) has been described from readily available raw materials. Sharpless asymmetric epoxidation and diastereoselective Barbier allylation of
Marco F Schmidt et al.
ChemMedChem, 8(1), 54-58 (2012-11-22)
Rational ligand design: Schaeffer's acid analogues were identified as novel inhibitors of M. tuberculosis type II dehydroquinase, a key enzyme of the shikimate pathway. Their likely binding mode was predicted using a combination of ensemble docking and flexible active site residues.

Questions

1–2 of 2 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

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