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S5375

Sigma-Aldrich

Shikimic acid

≥99%, suitable for ligand binding assays

Sinônimo(s):

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

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10 MG
R$ 318,00
1 G
R$ 1.113,00
5 G
R$ 5.839,00

R$ 318,00


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10 MG
R$ 318,00
1 G
R$ 1.113,00
5 G
R$ 5.839,00

About This Item

Fórmula empírica (Notação de Hill):
C7H10O5
Número CAS:
Peso molecular:
174.15
Beilstein:
2210055
Número CE:
Número MDL:
Código UNSPSC:
12352106
ID de substância PubChem:
NACRES:
NA.25

R$ 318,00


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Nome do produto

Shikimic acid, ≥99%

Ensaio

≥99%

Formulário

powder

técnica(s)

ligand binding assay: suitable

cor

white to off-white

pf

185-187 °C (lit.)

cadeia de caracteres SMILES

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

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

chave InChI

JXOHGGNKMLTUBP-HSUXUTPPSA-N

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Aplicação

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]

Ações bioquímicas/fisiológicas

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]

Pictogramas

Corrosion

Palavra indicadora

Danger

Frases de perigo

Declarações de precaução

Classificações de perigo

Eye Dam. 1

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)


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Inhibitory effects of shikimic acid on platelet aggragation and blood coagulation.
Ma Yi
Acta Pharmaceutica Sinica. B, 35, 1-3 (2000)
Efficient elimination of nonstoichiometric enzyme inhibitors from HTS hit lists.
Habig M
Journal of Biomolecular Screening, 14(6), 679-689 (2009)
Marco Krämer et al.
Metabolic engineering, 5(4), 277-283 (2003-12-04)
Shikimic acid is a high valued compound used as a key starting material for the synthesis of the neuramidase inhibitor GS4104, which was developed under the name Tamiflu for treatment of antiviral infections. An excellent alternative to the isolation of
Ruben Vanholme et al.
Science (New York, N.Y.), 341(6150), 1103-1106 (2013-08-21)
Lignin is a major component of plant secondary cell walls. Here we describe caffeoyl shikimate esterase (CSE) as an enzyme central to the lignin biosynthetic pathway. Arabidopsis thaliana cse mutants deposit less lignin than do wild-type plants, and the remaining
Kai Chen et al.
Bioresource technology, 119, 141-147 (2012-06-26)
Shikimic acid (SA) is an important metabolic intermediate with diverse commercial applications. In this work, antisense RNA interference and gene deletion were carried out to inactivate the aroK gene in an SA-producing Escherichia coli strain, DHPYA-T7. In this strain, the

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  1. 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

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  2. 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/449/386/product-dating-information-mk.pdf

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