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SMB01010

Marrubiin

≥90% (LC/MS-ELSD)

Synonym(s):

(1R,4S,8S,9R,10R,12R)-9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-2-oxatricyclo[6.3.1.04,12]dodecan-3-one

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About This Item

Empirical Formula (Hill Notation):
C20H28O4
CAS Number:
465-92-9
Molecular Weight:
332.43
UNSPSC Code:
12352205
NACRES:
NA.25
MDL number:
MFCD08461003
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biological source

plant

assay

≥90% (LC/MS-ELSD)

form

solid

mol wt

332.43

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

[o]1cc(cc1)CC[C@@]2([C@@]3([C@H]4[C@H](OC(=O)[C@]4(CCC3)C)C[C@H]2C)C)O

InChI

1S/C20H28O4/c1-13-11-15-16-18(2,17(21)24-15)7-4-8-19(16,3)20(13,22)9-5-14-6-10-23-12-14/h6,10,12-13,15-16,22H,4-5,7-9,11H2,1-3H3/t13-,15-,16+,18+,19+,20-/m1/s1

InChI key

HQLLRHCTVDVUJB-OBHOOXMTSA-N

General description

Marrubiin is a labdanoid lactone commonly derived from Marrubium Sp. plants, including M. globosum, M. alysson, M. vulgare, and M. anisodon. Existing research suggests that this plant-derived metabolite possesses various biological properties, including antioxidant, antifungal, gastroprotective, immunomodulatory, cardioprotective, anti-diabetic, and analgesic activities.

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

Based on existing research, Marrubiin has demonstrated the ability to inhibit the production of pro-inflammatory cytokines and reduce the activity of enzymes involved in oxidative stress. Additionally, it has been observed to lower blood pressure and provide protection against ischemic heart injury.

Features and Benefits

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

Other Notes

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pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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C Meyre-Silva et al.
Farmaco (Societa chimica italiana : 1989), 60(4), 321-326 (2005-04-26)
Marrubiin, a furane labdane diterpene, is the main analgesic compound present in Marrubium vulgare, a medicinal plant used in Brazil and other countries to treat several ailments. Considering its important pharmacological action, as well as its high yield, some structural