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C0625

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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Fórmula lineal:
(HO)2C6H3CH=CHCO2H
Número CAS:
Peso molecular:
180.16
UNSPSC Code:
12352106
NACRES:
NA.77
PubChem Substance ID:
EC Number:
206-361-2
Beilstein/REAXYS Number:
1954563
MDL number:
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Quality Level

assay

≥98.0% (HPLC)

form

powder

mp

211-213 °C (dec.) (lit.)

solubility

ethanol: 50 mg/mL

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

SMILES string

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+

InChI key

QAIPRVGONGVQAS-DUXPYHPUSA-N

Gene Information

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

General description

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.

Application

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. It has also been used to determine its antioxidant activity by various assay methods.

Biochem/physiol Actions

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. It non-competitively prevents the action of 5-lipoxygenase. Caffeic acid ready undergoes hydrolysis in alkaline conditions.

Features and Benefits

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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Este artículo
600182055468.22029
assay

≥98.0% (HPLC)

assay

≥99.0% (HPLC)

assay

≥95% (HPLC)

assay

≥98.0% (HPLC)

form

powder

form

powder

form

crystalline solid

form

powder

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

-

application(s)

-

application(s)

-

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

200

solubility

ethanol: 50 mg/mL

solubility

-

solubility

DMSO: 200 mg/mL, ethanol: 50 mg/mL

solubility

-

Gene Information

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

Gene Information

-

Gene Information

-

Gene Information

-


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Health hazard

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Hazard Classifications

Carc. 2

Clase de almacenamiento

11 - Combustible Solids

wgk

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flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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



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Comparing antioxidative food additives and secondary plant products-use of different assays
Kranl K, et al.
Food Chemistry, 93(1), 171-175 (2005)
Javier Cifuentes et al.
Antioxidants (Basel, Switzerland), 10(7) (2021-07-03)
Non-centrifugal cane sugar (NCS) is a traditional sweetener in most sugarcane regions of the world. In Colombia, this product has a socio-economic importance due to the extensive cultivation area and the high consumption rate per capita. NCS traditional processing involves
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)



Número de artículo de comercio global

SKUGTIN
C0625-2G04061835543090
C0625-25G04061835543083
C0625-5G04061835543106

Questions

1–3 of 3 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

      Helpful?

  2. Este producto podría considerarse un estándar de referencia o es sólo grado reactivo?

    1 answer
    1. This product is a research grade item. Note that the trans- isomer of this material, available as product 51868, is suitable for use as a Certified Reference Material. See the link below to review this product:
      https://www.sigmaaldrich.com/US/en/product/sial/51868

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  3. 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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