Rosmanol

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Structural formula
Structural formula of Rosmanol
General
Surname Rosmanol
other names

7α, 11,12-trihydroxy-6,10- (epoxymethano) abieta-8,11,13-trien-20-one ( IUPAC )

Molecular formula C 20 H 26 O 5
External identifiers / databases
CAS number 80225-53-2
PubChem 13966122
ChemSpider 10263992
Wikidata Q27277536
properties
Molar mass 346.42 g mol −1
Physical state

firmly

Melting point

241 ° C

safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Rosmanol is an organic compound belonging to the class of phenolic diterpenes . The compound was first described in 1981 after extraction from rosemary ( Rosmarinus officinalis ). An improved structure proposal was made by the same group in 1984.

Extraction

The compound occurs naturally in rosemary and sage, for example. An extract can be obtained from these by extraction using organic solvents such as n- hexane and subsequent steam distillation ; more modern methods of extraction are described, for example, using PLE or SFE . The extract is separated by obtaining the rosmanol by liquid chromatography such as HPLC-MS . Alternatively, the representation can take place starting from carnosic acid after conversion to carnosol by adding sodium hydrogen carbonate in acetone .

properties

The possible applications of this connection are currently the subject of research. In vitro , higher antioxidant properties could be demonstrated compared to carnosol . A contribution of the compound to the anti-inflammatory properties of rosemary cannot be ruled out either.

Individual evidence

  1. ↑ Reiko Inatani, Nobuji, Nakatani, Hidetsugu Fuwa: Antioxidative Effect of the Constituents of Rosemary (Rosmarinus officinalis L.) and Their Derivatives . In: Agric. Biol. Chem. Volume 47 , no. 3 , 1983, p. 521-528 , doi : 10.1080 / 00021369.1983.10865682 .
  2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  3. ↑ a b Nobuji Nakatani, Reiko Inatani: Structure of rosmanol, a new antixidant from rosmary . In: Agric. Biol. Chem. Volume 45 , no. 10 , 1981, pp. 2385-2386 , doi : 10.1080 / 00021369.1981.10864897 ( Open Access ).
  4. ↑ Nobuji Nakatani, Reiko Inatani: Two Antioxidative Diterpenes from Rosemary (Rosmarinus officinalis L.) and a Revised Structure for Rosmanol . In: Agric. Biol. Chem. Volume 48 , no. 8 , 1984, pp. 2081-2085 , doi : 10.1080 / 00021369.1984.10866436 ( Open Access ).
  5. ↑ M. Herrero, M. Plaza, A. Cifuentes, E. Ibáñez: Green processes for the extraction of bioactives from Rosemary: Chemical and functional characterization via ultra-performance liquid chromatography-tandem mass spectrometry and in-vitro assays . In: J. Chromatogr. A . tape 1217 , no. April 16 , 2010, p. 2512-2520 , doi : 10.1016 / j.chroma.2009.11.032 .
  6. ↑ a b F. J Señorans, E. Ibañez, S. Caver, J. Tabera, G. Regulator: Liquid chromatographic-mass spectrometric analysis of supercritical-fluid extracts of rosemary plants . In: J. Chromatogr. A . tape 870 , no. 1-2 , February 2000, pp. 491-499 , doi : 10.1016 / S0021-9673 (99) 00941-3 .
  7. ^ Marie Cuvelier, Claudette Berset, Hubert Richard: Antioxidant Constituents in Sage (Salvia officinalis) . In: J. Agric. Food Chem. Band 42 , no. 3 , March 1994, p. 665-669 , doi : 10.1021 / jf00039a012 .
  8. ↑ Joaquín G. Marrero, Lucía S. Andrés, Javier G. Luis: Semisynthesis of Rosmanol and Its Derivatives. Easy Access to Abietatriene Diterpenes Isolated from the Genus Salvia with Biological Activities . In: J. Nat. Prod. Band 65 , no. 7 , June 2002, p. 986-989 , doi : 10.1021 / np010565o .
  9. ↑ Sofía Cavero, Laura Jaime, Pedro J. Martín-Álvarez, F. Javier Señoráns, Guillermoglero, Elena Ibañez: In vitro antioxidant analysis of supercritical fluid extracts from rosemary . In: Eur. Food Res. Technol. tape 221 , no. 3–4 , August 2005, pp. 478-486 , doi : 10.1007 / s00217-005-1139-y .
  10. ^ Helle Lindberg Madsen, Grete Bertelesen: Spices as antioxidants . In: Trends in Food Science & Technology . tape 6 , no. 8 , August 1995, p. 271–277 , doi : 10.1016 / S0924-2244 (00) 89112-8 .
  11. ↑ Ching-Shu Lai, Jong Hun Lee, Chi-Tang Ho, Cheng Bin Liu, Ju-Ming Wang, Ying-Jan Wang, Min-Hsiung Pan: Rosmanol Potently Inhibits Lipopolysaccharide-Induced iNOS and COX-2 Expression through Downregulating MAPK, NF-κB, STAT3 and C / EBP Signaling Pathways . In: J. Agric. Food Chem. Band 57 , no. 22 , October 2009, p. 10990-10998 , doi : 10.1021 / jf9025713 .