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Merck
CN

SMB01002

Guineensine

≥90% (LC/MS-ELSD)

Synonym(s):

(2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-isobutyl-trideca-2,4,12-trienamide, Pipyahyine

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About This Item

Empirical Formula (Hill Notation):
C24H33NO3
CAS Number:
55038-30-7
Molecular Weight:
383.52
MDL number:
MFCD27967504
UNSPSC Code:
12352205
NACRES:
NA.25

Key Documents

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biological source

plant

Assay

≥90% (LC/MS-ELSD)

form

solid

mol wt

383.52

solubility

water: slightly soluble

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

N(CC(C)C)C(=O)\C=C\C=C\CCCCCC\C=C\c1cc2c(cc1)OCO2

InChI

1S/C24H33NO3/c1-20(2)18-25-24(26)14-12-10-8-6-4-3-5-7-9-11-13-21-15-16-22-23(17-21)28-19-27-22/h8,10-17,20H,3-7,9,18-19H2,1-2H3,(H,25,26)/b10-8+,13-11+,14-12+

InChI key

FPMPOFBEYSSYDQ-AUVZEZIHSA-N

Related Categories

General description

Guineensine, also known as Pipyahyine, is an alkaloid and a member of benzodioxoles is a natural product commonly available from Piper Sp.(P. nigrum and P. longum and P. retrofractum) plants. Existing research suggests that this plant-derived metabolite exerts various biological activities, including antimicrobial, anticancer, anti-inflammatory, antiviral and antioxidant properties.

Application

It is a natural product derived from plant source that finds application in compound screening libraries, metabolomics, phytochemical, and pharmaceutical research.

Biochem/physiol Actions

According to the existing research, Guineensine inhibits endocannabinoid uptake, leading to significant anti-inflammatory and analgesic effects, and also interacts with various receptors, including dopamine transporter DAT, 5HT2A, and sigma receptors, suggesting potential polypharmacological activity.

Features and Benefits

  • High quality compound suitable for multiple research applications
  • Compatible with HPLC and mass spectrometry techniques

Other Notes

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Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Ruben Bartholomäus et al.
ChemMedChem, 14(17), 1590-1596 (2019-07-20)
Guineensine ((2E,4E,12E)-13-(benzo[d][1,3]dioxol-5-yl)-N-isobutyltrideca-2,4,12-trienamide) is a plant-derived natural product that inhibits reuptake of the endocannabinoid anandamide with sub-micromolar potency. We have established a highly efficient total synthesis of guineensine, which provided the natural product in only five steps from commercially available 3-nonyn-1-ol

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