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Cinnamtannin A2

CAS: 86631-38-1

CAT: 5065

Abstract

Procyanidins are a sub class of proanthocyanidins (PACs), formed from (+) catechin and (-) epicatechin subunits. Procyanidins can be categorized into A-type and B-type, depending on the nature of the interflavan bonds. B-type procyanidins have a single interflavan bond. A-type procyanidins differentiate themselves from B-type procyanidins by containing a second interflavan bond between at least one set of subunits. The most abundant B-type tetrameric procyanidin is Cinnamtannin A2 ((−)-epicatechin tetramer,) (CAS 86631-38-1), which is found in popular dietary products such as apple skins, cocoa, and grapes.

Cinnamtannin A2 is being studied for a wide range of applications. It was reported to enhance GLP-1 and insulin secretion in mice, while also upregulating the expression of corticotrophin releasing hormone. It exhibits antioxidant, anti-diabetic, and nephroprotective effects. The compound has shown HIV-related and antioxidant activities. The epicatechin tetramer is also being studied for its ability to attenuate skeletal muscle disuse atrophy in mice. Dosage with the procyanidin tetramer have shown a shift to decreased muscle loss (Muta et al.).

The most significant dietary sources of the procyanidin tetramer are apples and cocoa products. However, roasted cocoa products tend to show significantly decreases in concentrations of Cinnamtannin A2 as well as other procyanidins.

You can find additional procyanidin reference standards here.

References

Withanoside IV and its active metabolite

Categories: Apple PACs, Cocoa PACs, Procyanidins (PACs)

Compound Details

CAS	86631-38-1
Molecular Weight	1155.0 g/mol
Chemical Formula	C₆₀H₅₀O₂₄
IUPAC	(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
SMILES	C1C(C(OC2=C1C(=CC(=C2C3C(C(OC4=C3C(=CC(=C4C5C(C(OC6=C(C(=CC(=C56)O)O)C7C(C(OC8=CC(=CC(=C78)O)O)C9=CC(=C(C=C9)O)O)O)C1=CC(=C(C=C1)O)O)O)O)O)C1=CC(=C(C=C1)O)O)O)O)O)C1=CC(=C(C=C1)O)O)O
Synonyms	Procyanidin Tetramer EEEE
Purity	95%+
Storage Temperature	Below −18°C
Storage Conditions	Dry, freezer

Product Documents

Certificates of Analysis

029-142-A

Safety Data Sheets

MSDS

$23.00 - $45.00 / milligram

Range (milligram)	Price ($/milligram)
5 - 24 milligram	$45.00 / milligram
25 - 99 milligram	$41.00 / milligram
100 - 249 milligram	$38.00 / milligram
250 - 499 milligram	$36.50 / milligram
500 - 1000 milligram	$23.00 / milligram

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Product information is from published literature. Due to the nature of scientific experimentation, results or specific product application may vary (e.g., selectivity, detector response). If you have questions about the product, its application, and associated analytics, please contact our technical support team.

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Products are sold as laboratory reference materials, to be used for diagnostic and in vivo testing. The samples are not certified for veterinary or human use.