Oleuropein

• CAS: 32619-42-4
• Catalog Number: ACM32619424
• Category: Inhibitors
• Molecular Weight: 540.51
• Molecular Formula: C25H32O13
• Description: Oleuropein, found in olive leaves and oil, exerts antioxidant, anti-inflammatory and anti-atherogenic effects through direct inhibition of PPARγ transcriptional activity. Oleuropein induces apoptosis in breast cancer cells via the p53-dependent pathway and through the regulation of Bax and Bcl2 genes. Oleuropein also inhibits aromatase.
• Synonyms: (2S)-3-[(E)-Ethylidene]-2-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2H-pyran-4α-acetic acid 2-(3,4-dihydroxyphenyl)ethyl ester
• IUPAC Name: Methyl (4S,5E,6S)-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl]-5-ethylidene-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
• Canonical SMILES: C/C=C/1\[C@@H](C(=CO[C@H]1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)OC)CC(=O)OCCC3=CC(=C(C=C3)O)O
• InChI: InChI=1S/C25H32O13/c1-3-13-14(9-19(29)35-7-6-12-4-5-16(27)17(28)8-12)15(23(33)34-2)11-36-24(13)38-25-22(32)21(31)20(30)18(10-26)37-25/h3-5,8,11,14,18,20-22,24-28,30-32H,6-7,9-10H2,1-2H3/b13-3+/t14-,18+,20+,21-,22+,24-,25-/m0/s1
• InChI Key: RFWGABANNQMHMZ-ZCHJGGQASA-N
• Boiling Point: 772.9±60.0 °C
• Melting Point: 89-90 °C
• Density: 1.50±0.1 g/ml
• Appearance: White powder
• Effective Constituent: Oleuropein
• pKa: 9.70±0.10
• Plant Origin: Olive tree

Custom Q&A

What is the molecular formula of Oleuropein?

The molecular formula of Oleuropein is C25H32O13.

What is the molecular weight of Oleuropein?

The molecular weight of Oleuropein is 540.5 g/mol.

What is the IUPAC name of Oleuropein?

The IUPAC name of Oleuropein is methyl (4S,5E,6S)-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl]-5-ethylidene-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate.

What are some synonyms of Oleuropein?

Some synonyms of Oleuropein are Oleoeuropein, oleoeuropeine, and 2-(3,4-Dihydroxyphenyl)ethyl (2S-(2alpha,3E,4beta))-3-ethylidene-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2H-pyran-4-acetate.

What organisms can Oleuropein be found in?

Oleuropein can be found in Jasminum officinale, Olea capensis, and other organisms.

What is the InChI of Oleuropein?

The InChI of Oleuropein is InChI=1S/C25H32O13/c1-3-13-14(9-19(29)35-7-6-12-4-5-16(27)17(28)8-12)15(23(33)34-2)11-36-24(13)38-25-22(32)21(31)20(30)18(10-26)37-25/h3-5,8,11,14,18,20-22,24-28,30-32H,6-7,9-10H2,1-2H3/b13-3+/t14-,18+,20+,21-,22+,24-,25-/m0/s1.

What is the Canonical SMILES of Oleuropein?

The Canonical SMILES of Oleuropein is CC=C1C(C(=COC1OC2C(C(C(C(O2)CO)O)O)O)C(=O)OC)CC(=O)OCCC3=CC(=C(C=C3)O)O.

What is the CAS number of Oleuropein?

The CAS number of Oleuropein is 32619-42-4.

What is the ChEMBL ID of Oleuropein?

The ChEMBL ID of Oleuropein is CHEMBL1911053.

What is the XLogP3-AA value of Oleuropein?

The XLogP3-AA value of Oleuropein is -0.4.

Synthetic Use

Downstream Synthesis Route 1

• 32619-42-4

• 35897-92-8

Reference: [1] European Journal of Medicinal Chemistry, 2017, vol. 137, p. 11 - 29

Downstream Synthesis Route 2

• 32619-42-4

• 60539-23-3

Reference: [1]Capozzi; Piperno; Uccella
[Journal of Agricultural and Food Chemistry, 2000, vol. 48, # 5, p. 1623 - 1629]
[2]Hanessian, Stephen; Mainetti, Emily; Lecomte, Fabien
[Organic Letters, 2006, vol. 8, # 18, p. 4047 - 4049]
[3]Samara, Pinelopi; Christoforidou, Nikoleta; Lemus, Christelle; Argyropoulou, Aikaterini; Ioannou, Kyriaki; Vougogiannopoulou, Konstantina; Aligiannis, Nektarios; Paronis, Efthimios; Gaboriaud-Kolar, Nicolas; Tsitsilonis, Ourania; Skaltsounis, Alexios-Leandros
[European Journal of Medicinal Chemistry, 2017, vol. 137, p. 11 - 29]

* For details of the synthesis route, please refer to the original source to ensure accuracy.