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Cnicin

$1,216

  • Brand : BIOFRON

  • Catalogue Number : BN-O1748

  • Specification : 98%(HPLC)

  • CAS number : 24394-09-0

  • Formula : C20H26O7

  • Molecular Weight : 378.4

  • PUBCHEM ID : 5281435

  • Volume : 10mg

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Catalogue Number

BN-O1748

Analysis Method

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

378.4

Appearance

Botanical Source

Structure Type

Category

SMILES

CC1=CCCC(=CC2C(C(C1)OC(=O)C(=C)C(CO)O)C(=C)C(=O)O2)CO

Synonyms

CYNISIN/cnicine/CENTAURIN

IUPAC Name

[(3aR,4S,6E,10Z,11aR)-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (3R)-3,4-dihydroxy-2-methylidenebutanoate

Density

1.27g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

219.1ºC

Boiling Point

622.3ºC at 760 mmHg

Melting Point

142-143ºC

InChl

InChl Key

ZTDFZLVUIVPZDU-QGNHJMHWSA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:24394-09-0) 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

24301356

Abstract

Water and solvent extracts from the aerial tissues ofCentaurea maculosa, spotted knapweed, inhibited the root growth of lettuce. Column chromatography and lettuce bioassay of a chloroform extract led to the isolation of cnicin, a sesquiterpene lactone. Pure cnicin was bioassayed at 0, 1, 2, 4, 6, 8, and 10 mg/5 ml water with lettuce, created wheatgrass, bluebunch wheatgrass, rough fescue, western larch, lodgepole pine, and spotted knapweed. Germination was inhibited at one or more concentrations for all species except lodgepole pine and spotted knapweed. Growth, particularly of the roots, was retarded between 1 and 4 mg of cnicin. Lettuce, bluebunch wheatgrass, and spotted knapweed were inhibited significantly at all concentrations tested.

Title

Phytotoxic properties of cnicin, a sesquiterpene lactone fromcentaurea maculosa (spotted knapweed).

Author

Kelsey RG1, Locken LJ.

Publish date

1987 Jan

PMID

24242206

Abstract

The sesquiterpene lactone cnicin was extracted fromCentaurea maculosa andCentaurea vallesiaca. We examined its effects on the ovipositional response and larval development of generalist and specialist insect herbivores associated withC. maculosa. For the oviposition trials, three plant species (C. maculosa, Achillea millefolium, andCichorium intybus), half of which were sprayed with 3% of cnicin, were exposed to the specialist mothsStenodes straminea, Agapeta zoegana, andPterolonche inspersa in field cages. All three species significantly preferredC. maculosa to other plants andP. inspersa significantly preferred cnicin-sprayed plants to untreated plants for oviposition. Tested over all species, cnicin significantly increased the number of eggs laid on a given plant. A larval diet test examined the toxicity of cnicin for larvae of the generalist noctuid mothSpodoptera littoralis. Cnicin concentrations of 3% and 6% were lethal and 1% and 0.5% seriously inhibited growth and development. The larvae of theC. maculosa specialistStenodes straminea survived at 6% cnicin, but none of the pupae hatched.Agapeta zoegana was able to survive at 1% and 3% cnicin. Both specialists had difficulties with the artificial diet, but weight increase and survival was not further reduced when cnicin was present compared with on the control diet. In conclusion, cnicin influenced host recognition by the specialist species, and larvae of the generalist did not survive on natural levels of cnicin. Growth and survival of the specialist were not influenced by cnicin but were considerably hampered on artificial diet.

Title

Influence of cnicin, a sesquiterpene lactone ofCentaurea maculosa (Asteraceae), on specialist and generalist insect herbivores.

Author

Landau I1, Muller-Scharer H, Ward PI.

Publish date

1994 Apr

PMID

18672863

Abstract

We present the X-ray structure of the antibacterial target enzyme MurA in complex with its substrate UNAG and the sesquiterpene lactone cnicin, a potent inhibitor of the enzyme. The structure reveals that MurA has catalyzed the formation of a covalent adduct between cnicin and UNAG. This adduct, which can be regarded as a noncovalent suicide inhibitor, has been formed by an unusual “anti-Michael” 1,3-addition of UNAG to an alpha,beta-unsaturated carbonyl function in cnicin.

Title

The unusual binding mode of cnicin to the antibacterial target enzyme MurA revealed by X-ray crystallography.

Author

Steinbach A1, Scheidig AJ, Klein CD.

Publish date

2008 Aug 28


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