16838-87-2

Basic information

• Product Name: zaluzanin C
• Synonyms: zaluzanin C;(3aβ,6aβ,9aβ,9bα)-3,6,9-Trismethylene-8α-hydroxydodecahydroazuleno[4,5-b]furan-2-one
• CAS NO: 16838-87-2
• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.304
• Mol File: 16838-87-2.mol

Chemical Properties

• Melting Point: 95-96 °C
• Boiling Point: 439.9°Cat760mmHg
• Flash Point: 189.9°C
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 1.38E-09mmHg at 25°C
• Refractive Index: 1.557
• PKA: 14.65±0.20(Predicted)
• CAS DataBase Reference: zaluzanin C(CAS DataBase Reference)
• NIST Chemistry Reference: zaluzanin C(16838-87-2)
• EPA Substance Registry System: zaluzanin C(16838-87-2)

Safety Data

• Hazardous Substances Data: 16838-87-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Zaluzanin C is used as a bioactive compound for its potential therapeutic properties. The specific chemical structure of zaluzanin C allows it to interact with various biological targets, making it a promising candidate for the development of new drugs and treatments.
Used in Cancer Research:
In the field of cancer research, zaluzanin C is used as a chemopreventive agent due to its ability to modulate multiple signaling pathways involved in cancer cell growth and progression. Its potential to inhibit tumor growth and induce apoptosis makes it a valuable tool in the search for novel cancer therapies.
Used in Drug Delivery Systems:
Similar to gallotannin, zaluzanin C can also be incorporated into drug delivery systems to enhance its bioavailability and therapeutic efficacy. By utilizing various organic and metallic nanoparticles as carriers, zaluzanin C can be more effectively delivered to target cells, improving its overall performance in treating specific conditions.

InChI:InChI=1/C15H18O3/c1-7-4-5-10-8(2)15(17)18-14(10)13-9(3)12(16)6-11(7)13/h10-14,16H,1-6H2

Upstream product

• 38236-17-8 isocostus lactone 
• 477-43-0 dehydrocostuslactone 
• 74299-48-2 dehydrocostus lactone 

Relevant articles and documents

Sesquiterpene lactones with potential use as natural herbicide models. 2. Guaianolides

A structure-activity study to evaluate the effect of 17 guaianolide sesquiterpene lactones (in a range of 100-0.001 μM) on the growth and germination of several mono- and dicotyledon target species is accomplished. Results are compared with those obtained in the same bioassay with an internal standard, the commercial herbicide Logran, to validate the results with a known active formulation and to compare the results with a commercial product to test their potential use as natural herbicide models. Specific conditions for the selective mono- or polyhydroxylation of guaianolides using the SeO2/tert-butyl hydroperoxide system are presented and discussed. The high regio- and stereo-selectivities of the reaction are explained through the specific structural requirements of the bulky first adduct formed during the ene reaction. These compounds appear to have deeper effects on the growth of either monocots or dicots than the previously tested germacranolides. Otherwise, the lactone group seems to be necessary for the activity, though it does not necessarily need to be unsaturated. However, the presence of a second and easily accessible unsaturated carbonyl system greatly enhances the inhibitory activity. Lipophilicity and the stereochemistry of the possible anchoring sites are also crucial factors for the activity. Finally, the levels of growth inhibition obtained with some compounds on dicots or monocots are totally comparable to those of Logran and allow proposing them as lead compounds.

Developing new herbicide models from allelochemicals

Plants contain allelochemicals which are their own defence systems and can act as herbicides. Selected examples of guaianolides and heliannuols, which are sesquiterpenes, are discussed in the context of their potential use as natural herbicide templates.

POTENTIAL ALLELOPATHIC ACTIVITY OF SEVERAL SESQUITERPENE LACTONE MODELS

A collection of 12 natural and synthetic sesquiterpene lactones with eudesmanolide, melampolide, cis,cis-germacranolide, and guaianolide skeletons have been prepared and tested as allelochemicals.The effect of a series of aqueous solutions at 10-4-10-9 M of this collection is evaluated.The specific structural requirements related to their activity is discussed.The natural sesquiterpene lactones soulangianolide A, melampomagnolide A and B, zaluzanin C and isozaluzanin C have been synthesized from costunolide, parthenolide and dehydrocostuslactone using SeO2 and tert-butylhydroperoxide.The structures of the synthetic compounds were established by NMR spectroscopy. Key Word Index - Sesquiterpene lactones; melampolides; cis,cis-germacranolides; guaianolides; eudesmanolides; allelopathy; Lactuca sativa.

Studies on the Syntheses of Sesquiterpene Lactones. 11. The Syntheses of 3-Epizaluzanin C, Zaluzanin C, Zaluzanin D, and Related Compounds 3&α-Hydroxyguaia-1(10),4(15),11(13)-trieno-12,6&α-lactone and 3&α-Hydroxyguaia-4(15),9,11(13)-trieno-12,6&α-lactone

3-Epizaluzanin C (10), 3α-hydroxyguaia-1(10),4(15),11(13)-trieno-12,6α-lactone (36), and 3α-hydroxyguaia-4(15),9,11(13)-trieno-12,6α-lactone (37) have been synthesized in 4.0percent, 3.0percent, and 1.7percent overall yields, respectively, from α-santonine (13) in 14 steps.Zaluzanin C (11) and zaluzanin D (12) have also been synthesized in 2.4percent and 2.5percent overall yields from α-santonin (13) in 16 steps and 15 steps, respectively.The key step involves the solvolytic rearrangement of (11S)-3α,4α-epoxy-1β-(mesyloxy)eudesmano-13,6α-lactone (27).The stereochemistry of3-epizaluzanin C (10), zaluzanin C (11), and zaluzanin D (12) have been established by these stereospecific syntheses.