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MW 354.31 Da, Purity >99%. Antioxidant with a variety of biological effects. Able to Inhibit DNA methylation catalysed by prokaryotic M.Sssl DNA methyltransferase and human DNMT1 (IC50 = 0.75 and 0.9 μM, respectively). Also able to stimulate glucose transport in skeletal muscle via AMPK activation.

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Images

Chemical Structure - Chlorogenic acid hemihydrate, Antioxidant (AB120973), expandable thumbnail

Key facts

CAS number
202650-88-2
Purity
> 99%
Form
Solid
Molecular weight
354.31 Da
Molecular formula
C16H18O9
PubChem identifier
1794427
Nature
Synthetic

Alternative names

Recommended products

MW 354.31 Da, Purity >99%. Antioxidant with a variety of biological effects. Able to Inhibit DNA methylation catalysed by prokaryotic M.Sssl DNA methyltransferase and human DNMT1 (IC50 = 0.75 and 0.9 μM, respectively). Also able to stimulate glucose transport in skeletal muscle via AMPK activation.

Key facts

Purity
> 99%
PubChem identifier
1794427
Solubility

Soluble in water to 25 mM.

Biochemical name
Chlorogenic acid
Biological description

Antioxidant with a variety of biological effects. Able to Inhibit DNA methylation catalysed by prokaryotic M.Sssl DNA methyltransferase and human DNMT1 (IC50 = 0.75 and 0.9 μM, respectively). Also able to stimulate glucose transport in skeletal muscle via AMPK activation.

Canonical SMILES
C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)O
Isomeric SMILES
C1[C@H]([C@H]([C@@H](C[C@@]1(C(=O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)O
InChI
InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1
InChIKey
CWVRJTMFETXNAD-JUHZACGLSA-N
IUPAC name
(1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid

Storage

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
+4°C
Appropriate long-term storage conditions
+4°C
Storage information
The product can be stored for up to 12 months

Supplementary info

This supplementary information is collated from multiple sources and compiled automatically.
Activity summary

PTP1B also known as Protein Tyrosine Phosphatase 1B is an enzyme with a mass of approximately 50 kDa. This protein serves as a negative regulator of insulin and leptin signaling pathways and is widespread in tissues like liver muscle and adipose tissue. Its enzymatic action involves dephosphorylation of tyrosine residues in target proteins which reduces activity in insulin signaling. PTP1B is an essential modulator of energy metabolism and plays vital roles in regulating glucose and lipid homeostasis.

Biological function summary

PTP1B participates in processes that involve insulin resistance and energy balance but it does not directly form part of a larger protein complex. Aldose reductase another enzyme is distinct yet often discussed alongside PTP1B because of its role in the polyol pathway where it reduces glucose to sorbitol and can under certain conditions contribute to diabetic complications. Aldose reductase is a cytosolic enzyme ubiquitously expressed especially in lens renal cortex and peripheral nerves and has a mass of about 36 kDa. It serves as a catalytic converter of aldehydes to alcohols and therefore modulates osmotic balance by reducing harmful aldehyde accumulation.

Pathways

PTP1B is a significant player in the insulin and leptin signaling pathways. These pathways are critical for cellular functions and energy regulation. The insulin signaling pathway involves proteins such as IRS-1 (Insulin Receptor Substrate-1). Within these pathways PTP1B's action leads to reduction of insulin receptor activity impacting downstream signaling events necessary for glucose uptake and energy balance. Aldose reductase fits into the polyol pathway where sorbitol accumulation can lead to diabetic complications. This pathway involves NADPH as a cofactor and is an important player in glucose metabolism.

Associated diseases and disorders

Both PTP1B and aldose reductase are implicated in type 2 diabetes and its complications such as diabetic retinopathy. PTP1B through its modulation of insulin signaling impacts insulin resistance a hallmark of type 2 diabetes. Its activity is linked to disorders in glucose metabolism often associated with elevated levels in obese and insulin-resistant individuals. Aldose reductase is related to hyperglycemic damage in diabetic patients as its overactivity can lead to sorbitol accumulation causing osmotic and oxidative stress. Connections between PTP1B and proteins in insulin signaling pathways such as the insulin receptor further underpin its role in these metabolic disorders.

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1 product image

  • Chemical Structure - Chlorogenic acid hemihydrate, Antioxidant (ab120973), expandable thumbnail

    Chemical Structure - Chlorogenic acid hemihydrate, Antioxidant (ab120973)

    2D chemical structure image of ab120973, Chlorogenic acid hemihydrate, Antioxidant

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