marrubiin
2H-naphtho(1,8-bc)furan-2-one, 6-(2-(3-furanyl)ethyl)decahydro-6-hydroxy-2a,5a,7-trimethyl-, (2aS-(2aalpha,5abeta,6alpha,7alpha,8aalpha,8balpha))-
Identification
| Name | marrubiin |
| CAS Number | 465-92-9 |
| FDA UNII | AP086P88M4 |
| Molecular Formula | C20 H28 O4 |
| Molecular Weight | 332.43996000 |
| MDL Number | MFCD08461003 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 465.20 °C. @ 760.00 mm Hg (est) |
| Flash Point | 455.00 °F. TCC ( 235.20 °C. ) (est) |
| logP (o/w) | 3.400 (est) |
| Soluble in | water, 8.391 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for marrubiin usage levels up to | not for fragrance use. |
| Recommendation for marrubiin flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
15,16-
epoxy-6b,9-dihydroxy-8bH-labda-13(16),14-dien-19-oic Acid g-Lactone
(2aS,5aS,6R,7R,8aR,8bR)-6-[2-(3-
furyl)ethyl]-6-hydroxy-2a,5a,7-trimethyldecahydro-2H-naphtho[1,8-bc]furan-2-one
2H-
naphtho(1,8-bc)furan-2-one, 6-(2-(3-furanyl)ethyl)decahydro-6-hydroxy-2a,5a,7-trimethyl-, (2aS-(2aalpha,5abeta,6alpha,7alpha,8aalpha,8balpha))-
PubMed:
Diterpene synthases of the biosynthetic system of medicinally active diterpenoids in Marrubium vulgare.
PubMed:
Marrubiin.
PubMed:
Spiraeamide, new sphingolipid from Spiraea brahuica.
PubMed:
Marrubiin, a constituent of Leonotis leonurus, alleviates diabetic symptoms.
PubMed:
Vasodilator effect of Phlomis bracteosa constituents is mediated through dual endothelium-dependent and endothelium-independent pathways.
PubMed:
Antioxidant and antigenotoxic properties of compounds isolated from Marrubium deserti de Noé.
PubMed:
The cardioprotective effects of marrubiin, a diterpenoid found in Leonotis leonurus extracts.
PubMed:
Gastroprotective activity of methanol extract and marrubiin obtained from leaves of Marrubium vulgare L. (Lamiaceae).
PubMed:
[Studies on chemical constituents of Eriophyton wallichii].
PubMed:
Accumulation of furanic labdane diterpenes in Marrubium vulgare and Leonurus cardiaca.
PubMed:
Antioedematogenic effect of marrubiin obtained from Marrubium vulgare.
PubMed:
Analgesic potential of marrubiin derivatives, a bioactive diterpene present in Marrubium vulgare (Lamiaceae).
PubMed:
The vasorelaxant activity of marrubenol and marrubiin from Marrubium vulgare.
PubMed:
Labdane diterpenoids from Marrubium globosum ssp. globosum.
PubMed:
Analysis of the antinociceptive properties of marrubiin isolated from Marrubium vulgare.
PubMed:
Biosynthesis of the labdane diterpene marrubiin in Marrubium vulgare via a non-mevalonate pathway.
PubMed:
[Chemical tests with Marrubium species. Official data on Marubii herba in Pharmacopoeia Hungarica VII].
PubMed:
The role of general metabolites in the biosynthesis of natural products. IV. Incorporation of U-14C ribose and U-14C fructose in marrubiin terpene.
PubMed:
The role of general metabolites in the biosynthesis of natural products. I. The terpene marrubiin.
PubMed:
Stereochemistry of marrubiin.
PubMed:
Some preliminary work on the synthesis of marrubiin.