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Merck

C0625

Sigma-Aldrich

Caffeic acid

≥98.0% (HPLC)

Sinónimos:

3,4-Dihydroxybenzeneacrylic acid, 3,4-Dihydroxycinnamic acid, 3-(3,4-Dihydroxyphenyl)-2-propenoic acid

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2 G
$102.000
5 G
$162.000
25 G
$354.000

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2 G
$102.000
5 G
$162.000
25 G
$354.000

About This Item

Fórmula lineal:
(HO)2C6H3CH=CHCO2H
Número de CAS:
Peso molecular:
180.16
Beilstein:
1954563
Número CE:
Número MDL:
Código UNSPSC:
12352106
ID de la sustancia en PubChem:
NACRES:
NA.77

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Nivel de calidad

Ensayo

≥98.0% (HPLC)

Formulario

powder

mp

211-213 °C (dec.) (lit.)

solubilidad

ethanol: 50 mg/mL

aplicaciones

metabolomics
vitamins, nutraceuticals, and natural products

cadena SMILES

OC(=O)\C=C\c1ccc(O)c(O)c1

InChI

1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+

Clave InChI

QAIPRVGONGVQAS-DUXPYHPUSA-N

Información sobre el gen

human ... ELA2(1991)
rat ... Alox5(25290)

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Descripción general

Caffeic acid exists in its free and ester form. It is considered as the predominant polyphenol, contributing to the hydroxycinnamic acid content in various fruits. Coffee is one of the major source of caffeic acid.[1]

Aplicación

Caffeic acid has been used as a standard of phenolic acid in the study to determine the total phenolic acid content in vegetables after subjecting to alkaline and acid hydrolysis.[2] It has also been used to determine its antioxidant activity by various assay methods.[3]

Acciones bioquímicas o fisiológicas

A natural dietary phenolic compound found in plants that is an anti-oxidant. Inhibits the synthesis of leukotrienes that are involved in immunoregulation, inflammation and allergy. Inhibits Cu2+-induced LDL oxidation.
Anti-oxidant phenolic compound found in plants; Inhibits the synthesis of leukotrienes.
Caffeic acid and other polyphenols are metabolized by going through enzyme catalysed methyl transfer, sulfation and glucuronic acid addition.[1] It non-competitively prevents the action of 5-lipoxygenase.[4] Caffeic acid ready undergoes hydrolysis in alkaline conditions.[2]

Características y beneficios

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

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Descripción
Precios

Pictogramas

Health hazard

Palabra de señalización

Warning

Frases de peligro

Clasificaciones de peligro

Carc. 2

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges


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Comparing antioxidative food additives and secondary plant products-use of different assays
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Food Chemistry, 93(1), 171-175 (2005)
Caffeic acid is a selective inhibitor for leukotriene biosynthesis
Yasuko K, et al.
Biochimica et Biophysica Acta, Lipids and Lipid Metabolism, 792(1), 92-97 (1984)
Polyphenols: food sources and bioavailability
Manach C, et al.
American Journal of Clinical Nutrition, 79(5), 727-747 (2004)
Phenolic acids in potatoes, vegetables, and some of their products
Mattila P and Hellstrom J
J. Food Compos. Anal., 20(3-4), 152-160 (2007)
B Y Hsu et al.
Journal of pharmaceutical and biomedical analysis, 132, 109-116 (2016-10-05)
A high performance liquid chromatography-diode array detection-tandem mass spectrometry method (HPLC-DAD-MS/MS) was developed for simultaneous determination of phenolic acids and flavonoids in djulis (Chenopodium formosanum Koidz.), a traditional Chinese herb reported to possess vital biological activities. A high yield of

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DISCOVER Bioactive Small Molecules for Nitric Oxide & Cell Stress Research

We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.

Protocolos

HPLC Analysis of Polyphenols in Nero d'Avola Red Wine on Discovery® HS C18 (UV 280 nm)

Protocol for HPLC Analysis of Flavonoids on Ascentis® RP-Amide

Questions

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  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/449/386/product-dating-information-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

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