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(S)-(+)-Carvone

$52

  • Brand : BIOFRON

  • Catalogue Number : BD-D1257

  • Specification : 98%(HPLC)

  • CAS number : 2244-16-8

  • Formula : C10H14O

  • Molecular Weight : 150.22

  • Volume : 0.1ML

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Catalogue Number

BD-D1257

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

150.22

Appearance

liquid

Botanical Source

Structure Type

Monoterpenoids

Category

SMILES

Synonyms

IUPAC Name

Applications

Density

0.9±0.1 g/cm3

Solubility

Flash Point

88.9±0.0 °C

Boiling Point

230.5±35.0 °C at 760 mmHg

Melting Point

88.9ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2914290000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:2244-16-8) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

31419501

Abstract

Ethnopharmacological relevance: Lippia alnifolia Mart. & Schauer, known as “alecrim-do-mato”, “alecrim-de-vaqueiro” and “pedrecio”, is used in folk medicine as antiseptic and to treat diseases that affect respiratory system, like bronchitis and asthma.

Aim of the study: The aim of this work was to investigate the spasmolytic activity and relaxant mechanism of the Lippia alnifolia essential oil (EOLA) on isolated guinea-pig trachea and to correlate with its use in folk medicine.

Materials and methods: Leaves from L. alnifolia were collected in Pico das Almas, Chapada Diamantina, situated in the city of Rio de Contas, Bahia, Brazil. EOLA was extracted by hydrodistillation, analyzed by GC/FID and GC/MS and the volatile constituents were identified. Spasmolytic activity was assayed in isolated guinea-pig trachea pre-contracted with carbachol 1 μM or histamine 10 μM. Relaxant mechanism of EOLA was determined comparing concentration-response curves in the presence or absence of different blockers.

Results: Chemical analysis revealed the presence of carvone (60 ± 0.8%) as major constituent. EOLA (1-243 μg/mL) relaxed isolated guinea-pig trachea pre-contracted with carbachol 1 μM [EC50 = 53.36 (44.75-63.51) μg/mL] or histamine 10 μM [EC50 = 5.42 (4.42-6.65) μg/mL]. The pre-incubation of 4-aminopyridine in histamine-induced contractions did not alter significantly the relaxant effect of EOLA. However, the presence of cesium chloride, glibenclamide, tetraethylammonium, propranolol, indomethacin, dexamethasone, hexamethonium, atropine, L-NAME, methylene blue or ODQ reduced EOLA relaxant effect. EOLA 18 μg/mL pre-incubation in calcium-free medium reduced histamine-evoked contractions, but did not alter histamine contractions in the presence of nifedipine.

Conclusions: Lippia alnifolia essential oil has spasmolytic activity on isolated guinea-pig trachea and its mechanism of action possibly involves the activation of multiple signal transduction pathways, which culminate in potassium channels activation and cytosolic calcium reduction.

KEYWORDS

Potassium channels; Prostanoids; Spasmolytic activity; Terpenoids; Verbenaceae.

Title

Lippia alnifolia essential oil induces relaxation on Guinea-pig trachea by multiple pathways

Author

Deisy Azevedo Dourado Vilela 1, Bismarques Augusto Oliveira Silva 2, Mariana Coelho Brito 3, Pedro Modesto Nascimento Menezes 4, Horacio Freitas Bomfim 5, Luiz Antonio Miranda de Souza Duarte-Filho 6, Tania Regina Dos Santos Silva 7, Luciano Augusto de Araújo Ribeiro 8, Angelica Maria Lucchese 9, Fabricio Souza Silva 10

Publish date

2020 Jan 10;

PMID

31336938

Abstract

(2R,5R)-dihydrocarvone is an industrially applied building block that can be synthesized by site-selective and stereo-selective C=C bond bio-reduction of (R)-carvone. Escherichia coli (E. coli) cells overexpressing an ene reductase from Nostoc sp. PCC7120 (NostocER1) in combination with a cosubstrate regeneration system proved to be very effective biocatalysts for this reaction. However, the industrial applicability of biocatalysts is strongly linked to the catalysts’ activity. Since the cell-internal NADH concentrations are around 20-fold higher than the NADPH concentrations, we produced E. coli cells where the NADPH-preferring NostocER1 was exchanged with three different NADH-accepting NostocER1 mutants. These E. coli whole-cell biocatalysts were used in batch operated stirred-tank reactors on a 0.7 l-scale for the reduction of 300 mM (R)-carvone. 287 mM (2R,5R)-dihydrocarvone were formed within 5 h with a diasteromeric excess of 95.4% and a yield of 95.6%. Thus, the whole-cell biocatalysts were strongly improved by using NADH-accepting enzymes, resulting in an up to 2.1-fold increased initial product formation rate leading to a 1.8-fold increased space-time yield when compared to literature.

KEYWORDS

(2R,5R)-dihydrocarvone; (R)-carvone; asymmetric reduction; biotransformation; ene reductase; formate dehydrogenase.

Title

Asymmetric Whole-Cell Bio-Reductions of ( R)-Carvone Using Optimized Ene Reductases

Author

Christoph Mahler 1, Christian Burger 1, Franziska Kratzl 1, Dirk Weuster-Botz 1, Kathrin Castiglione 2

Publish date

2019 Jul 12;

PMID

31111291

Abstract

Different enantiomers of chiral compounds within floral perfumes usually trigger distinct responses in insects; however, this has frequently been neglected in studies investigating semiochemicals in plant-pollinator interactions. Approximately 1000 neotropical plants produce floral perfumes as the only reward for pollinators, i.e. male euglossine bees. The chiral compound carvone epoxide is a key component of the scent bouquet of many perfume-rewarding plants that are pollinated by males of Eulaema. Here, we tested the biological activity of the four carvone epoxide stereoisomers to four Eulaema species occurring in the Atlantic Rainforest of NE-Brazil. We determined the stereochemistry of carvone epoxide in the floral scent of several Catasetum species, tested whether the antennae of bees respond differentially to these stereoisomers and investigated if there is a behavioural preference for any of the stereoisomers. We found that 1) Catasetum species emit only the (-)-trans-stereoisomer of carvone epoxide, 2) for E. atleticana and E. niveofasciata antennal responses to the (-)-trans-carvone epoxide were significantly stronger than those to (-)-cis-carvone epoxide, 3) the strength and pattern of antennal responses to all 4 stereoisomers (separately tested) did not differ among Eulaema species, and 4) there were significant differences in attractiveness of the four stereoisomers to the bees species with the (-)-trans-stereoisomer being particularly attractive. We assume (-)-trans-carvone epoxide to be the dominant isomer in perfume-rewarding plants pollinated by Eulaema. The universal occurrence of carvone epoxide in Catasetum species pollinated by Eulaema, suggests that this compound has evolved in perfume-rewarding as a specific attractant for Eulaema bees as pollinators.

KEYWORDS

Catasetum; Chirality; Electrophysiology; Euglossine bees; Eulaema; Perfume-rewarding plants; Pollinators.

Title

Subtle Chemical Variations with Strong Ecological Significance: Stereoselective Responses of Male Orchid Bees to Stereoisomers of Carvone Epoxide

Author

Katharina Brandt 1, Stefan Dotterl 2, Roman Fuchs 2, Daniela Maria do Amaral Ferraz Navarro 3, Isabel Cristina Sobreira Machado 4, Daniel Dobler 5, Oliver Reiser 5, Manfred Ayasse 1, Paulo Milet-Pinheiro 6

Publish date

2019 Jun