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65969

4-O-Caffeoylquinic acid

≥98.0%

Synonym(s):

4-O-(3,4-Dihydroxycinnamoyl)-D-quinic acid, Cryptochlorogenic acid

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About This Item

Empirical Formula (Hill Notation):
C16H18O9
CAS Number:
Molecular Weight:
354.31
NACRES:
NA.28
PubChem Substance ID:
UNSPSC Code:
12352204
MDL number:
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Quality Segment

assay

≥98.0%

form

powder or crystals

optical activity

[α]/D -76.0±5.0°, c = 0.5 in H2O

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

O[C@@H]1C[C@](O)(C[C@@H](O)[C@@H]1OC(=O)\C=C\c2ccc(O)c(O)c2)C(O)=O

InChI

1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(21)25-14-11(19)6-16(24,15(22)23)7-12(14)20/h1-5,11-12,14,17-20,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1

InChI key

GYFFKZTYYAFCTR-JUHZACGLSA-N

General description

It is an ester of caffeic acid and quinic acid.[1]
4-caffeoylquinic acid (4-CQA) is the derivative of caffeic acid (CA).

Application

4-O-Caffeoylquinic acid has been used as a reference compound for the quantification in high performance liquid chromatography-diode array detector (HPLC-DAD).

Biochem/physiol Actions

4-O-Caffeoylquinic acid (4-CQA) is a major active antioxidant marker in mulberry leaf extract.[2] It is an inhibitor of ferroptosis hence, it is recognized as a potent anti-diabetic agent.[3] 4-CQA plays an important role in the upregulation of nuclear factor (erythroid-derived 2)-like 2 (Nrf2) pathway.[1]

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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This Item
SMB00221SMB00224SMB00131
assay

≥98.0%

assay

≥85% (LC/MS-ELSD)

assay

≥90% (LC/MS-ELSD)

assay

≥95% (LC/MS-ELSD)

form

powder or crystals

form

solid

form

solid

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

optical activity

[α]/D -76.0±5.0°, c = 0.5 in H2O

optical activity

-

optical activity

-

optical activity

-


Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable



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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

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