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Oleuropein information


Oleuropein
Names
IUPAC name
Methyl (2S,3E,4S)-4-{2-[2-(3,4-Dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-(β-D-glucopyranosyloxy)-2H-pyran-5-carboxylate
Systematic IUPAC name
Methyl (2S,3E,4S)-4-{2-[2-(3,4-Dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-pyran-5-carboxylate
Other names
2-(3,4-Dihydroxyphenyl)ethyl [(2S,3E,4S)-3-ethylidene-2-(β-D-glucopyranosyloxy)-5-(methoxycarbonyl)-3,4-dihydro-2H-pyran-4-yl]acetate
Identifiers
CAS Number
  • 32619-42-4 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL1911053 ☒N
ChemSpider
  • 4444876 checkY
ECHA InfoCard 100.046.466 Edit this at Wikidata
PubChem CID
  • 5281544
UNII
  • 2O4553545L checkY
CompTox Dashboard (EPA)
  • DTXSID60905103 Edit this at Wikidata
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 checkY
    Key: RFWGABANNQMHMZ-ZCHJGGQASA-N checkY
  • InChI=1/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
    Key: RFWGABANNQMHMZ-ZCHJGGQABE
SMILES
  • O=C(OCCc1ccc(O)c(O)c1)C[C@H]2C(=C/C)\[C@@H](O\C=C2\C(=O)OC)O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)CO
Properties
Chemical formula
C25H32O13
Molar mass 540.518 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Oleuropein is a glycosylated seco-iridoid, a type of phenolic bitter compound found in green olive skin, flesh, seeds, and leaves.[1] The term oleuropein is derived from the botanical name of the olive tree, Olea europaea.

Because of its bitter taste, oleuropein must be completely removed or decomposed to make olives edible. During processing of bitter and inedible green olives for consumption as table olives, oleuropein is removed from olives via a number of methods, including by immersion in lye.[2][3]

  1. ^ Rupp R. (1 July 2016). "The bitter truth about olives". National Geographic. Archived from the original on 10 July 2019. Retrieved 24 June 2019.
  2. ^ "How olives are made". California Olive Committee. 2017. Archived from the original on 5 August 2017. Retrieved 5 August 2017.
  3. ^ Colmagro S.; Collins G.; Sedgley M. "Processing technology of the table olive" (PDF). Archived (PDF) from the original on 9 August 2017. Retrieved 25 June 2019.

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Oleuropein

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Oleuropein is a glycosylated seco-iridoid, a type of phenolic bitter compound found in green olive skin, flesh, seeds, and leaves. The term oleuropein...

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Hydroxytyrosol

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leaves, and olive pulp contain large amounts of hydroxytyrosol derivative Oleuropein, more so than olive oil. Unprocessed, green (unripe) olives, contain between...

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Olive

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brown or black. To leach the oleuropein from olives, commercial producers use lye, which neutralizes the bitterness of oleuropein, producing a mild flavour...

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Olive leaf

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extra virgin olive oil. Chemical compounds in unprocessed olive leaf are oleuropein and hydroxytyrosol, as well as polyphenols and flavonoids, including luteolin...

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Syringa

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Syringa include phenylpropanoids such as syringin and iridoids such as oleuropein. Substituent compounds, such as iridoids, as well as crude extracts from...

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Oleocanthal

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Oleocanthal is a tyrosol ester and its chemical structure is related to oleuropein, also found in olive oil. Oleocanthal has been found to have anti-inflammatory...

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Iridoid

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cyclopentane ring gives rise to a subclass known as secoiridoids, such as oleuropein and amarogentin. The iridoids produced by plants act primarily as a defense...

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Ligstroside

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role as a plant metabolite and an antineoplastic agent. Differs from oleuropein by one hydroxyl group. "ligstroside (CHEBI:149585)". www.ebi.ac.uk. Montedoro...

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Argan oil

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carotenes, squalene. Some trace phenols in argan oil include caffeic acid, oleuropein, vanillic acid, tyrosol, catechol, resorcinol, (−)-epicatechin and (+)-catechin...

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Aglycone

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Luccarini I, Traini C, et al. (2013-08-08). Ohno M (ed.). "The polyphenol oleuropein aglycone protects TgCRND8 mice against Aß plaque pathology". PLOS ONE...

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Olive oil

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(about 0.5%), such as esters of tyrosol, hydroxytyrosol, oleocanthal and oleuropein, which give extra virgin olive oil its bitter, pungent taste, and are...

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Capsaicin

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Polyphenols Aromatic acids Phenylethanoids Tyrosol Hydroxytyrosol Oleocanthal Oleuropein Others Capsaicin Gingerol Alkylresorcinols Misc: Phenolic compounds Phlorotannins)...

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Manzanilla olive

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Curing is a process to remove bitter phenolic compounds that include oleuropein and ligstroside found in the flesh and skin. Manzanillas have been a popular...

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Bisphenol A

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GPER-L1 GPER-L2 Hydroxytyrosol Kepone Niacin Niacinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol...

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Elenolic acid

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leaf extract. It can be considered as a marker for maturation of olives. Oleuropein, a chemical compound found in olive leaf from the olive tree, together...

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Spironolactone

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GPER-L1 GPER-L2 Hydroxytyrosol Kepone Niacin Niacinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol...

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DDT

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GPER-L1 GPER-L2 Hydroxytyrosol Kepone Niacin Niacinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol...

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Nicotinamide

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GPER-L1 GPER-L2 Hydroxytyrosol Kepone Niacin Niacinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol...

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Steroid

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GPER-L1 GPER-L2 Hydroxytyrosol Kepone Niacin Niacinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol...

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Enclomifene

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GPER-L1 GPER-L2 Hydroxytyrosol Kepone Niacin Niacinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol...

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Flavonoid

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Polyphenols Aromatic acids Phenylethanoids Tyrosol Hydroxytyrosol Oleocanthal Oleuropein Others Capsaicin Gingerol Alkylresorcinols Misc: Phenolic compounds Phlorotannins)...

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Quercetin

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GPER-L1 GPER-L2 Hydroxytyrosol Kepone Niacin Niacinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol...

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Dihydrotestosterone

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GPER-L1 GPER-L2 Hydroxytyrosol Kepone Niacin Niacinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol...

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Testosterone

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Betalain

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Polyphenols Aromatic acids Phenylethanoids Tyrosol Hydroxytyrosol Oleocanthal Oleuropein Others Capsaicin Gingerol Alkylresorcinols Misc: Phenolic compounds Phlorotannins)...

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Dietary fiber

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Polyphenols Aromatic acids Phenylethanoids Tyrosol Hydroxytyrosol Oleocanthal Oleuropein Others Capsaicin Gingerol Alkylresorcinols Misc: Phenolic compounds Phlorotannins)...

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Clomifene

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GPER-L1 GPER-L2 Hydroxytyrosol Kepone Niacin Niacinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol...

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Phenylpropanoid

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Polyphenols Aromatic acids Phenylethanoids Tyrosol Hydroxytyrosol Oleocanthal Oleuropein Others Capsaicin Gingerol Alkylresorcinols Misc: Phenolic compounds Phlorotannins)...

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Estrogen

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GPER-L1 GPER-L2 Hydroxytyrosol Kepone Niacin Niacinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol...

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