75088-80-1

Basic information

• Product Name: MANOALIDE
• Synonyms: MANOALIDE;MANOALIDE, LUFFARIELLA VARIABILIS;4-[3,6-DIHYDRO-6-HYDROXY-5-[4-METHYL-6-(2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL)-3-HEXENYL]-2H-PYRAN-2-YL]-5-HYDROXY-2(5H)-FURANONE;(5R)-4-[(2R,6R)-3,6-Dihydro-6-hydroxy-5-[4-methyl-6-(2,6,6-trimethyl-1-cyclohexene-1-yl)-3-hexenyl]-2H-pyran-2-yl]-5-hydroxyfuran-2(5H)-one;2(5H)-Furanone, 4-((2R,6R)-3,6-dihydro-6-hydroxy-5-((3E)-4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-hexenyl)-2H-pyran-2-yl)-5-hydroxy-, (5R)-;2(5H)-Furanone, 4-(3,6-dihydro-6-hydroxy-5-(4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-hexenyl)-2H-pyran-2-yl)-5-hydroxy-
• CAS NO: 75088-80-1
• Molecular Formula: C₂₅H₃₆O₅
• Molecular Weight: 416.55
• Mol File: 75088-80-1.mol

Chemical Properties

• Boiling Point: 609.6°C at 760 mmHg
• Flash Point: 203.3°C
• Appearance: tan/oil
• Density: 1.133g/cm³
• Vapor Pressure: 2.08E-17mmHg at 25°C
• Refractive Index: 1.549
• Storage Temp.: −20°C
• PKA: 9.75±0.40(Predicted)
• CAS DataBase Reference: MANOALIDE(CAS DataBase Reference)
• NIST Chemistry Reference: MANOALIDE(75088-80-1)
• EPA Substance Registry System: MANOALIDE(75088-80-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/22
• Safety Statements: 36
• WGK Germany: 3
• Hazardous Substances Data: 75088-80-1(Hazardous Substances Data)

Usage

Uses

Manoalide is a potent inhibitor of PLC, PLA2, and calcium channel proteins.

Definition

ChEBI: A sesterterpenoid isolated from the marine sponge Luffariella variabilis and which has been shown to exhibit inhibitory activity towards phospholipase A2.

InChI:InChI=1/C25H36O5/c1-16(10-12-20-17(2)8-6-14-25(20,3)4)7-5-9-18-11-13-21(29-23(18)27)19-15-22(26)30-24(19)28/h7,11,15,21,23-24,27-28H,5-6,8-10,12-14H2,1-4H3/b16-7+/t21-,23-,24-/m1/s1

Upstream product

• 110202-12-5 2-trimethylsilyl-4-<(3E,7E)-10-(2,6,6-trimethyl-1-cyclohexen-1-yl)-8-methyl-4-formyl-1-hydroxy-3,7-decadien-1-yl>-furan 
• 17283-81-7 4-(2,6,6-Trimethyl-cyclohex-1-enyl)-butan-2-on 
• 110202-10-3 (E)-2-Eth-(E)-ylidene-6-methyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-oct-5-enal 
• 110202-09-0 1-bromo-4-methyl-6-(2,6,6-trimethylcyclohex-1-enyl)-3-hexene 
• 214421-61-1 (E)-2-[3-Hydroxy-3-[5-oxo-2-(2-trimethylsilanyl-ethoxy)-2,5-dihydro-furan-3-yl]-prop-(E)-ylidene]-6-methyl-8-(trimethyl-cyclohex-1-enyl)-oct-5-enal 
• 130493-22-0 5-Triethylsilyl-3-furaldehyde 
• 498-60-2 furan-3-carboxaldehyde 
• 4179-00-4 Methyl (E)-3-methyl-5-(2,6,6-trimethylcyclohexen-1-yl)-2-pentenoate 
• 18665-81-1 (E)-3-methyl-5-(2',6',6'-trimethylcyclohex-1'-en-1'-yl)pent-2-en-1-ol 
• 29550-53-6 (E)-3-methyl-5-(2',6',6'-trimethylcyclohex-1'-enyl)pent-2-enyl bromide 
• 110202-11-4 Trimethyl-[(1Z,5E)-6-methyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-2-vinyl-octa-1,5-dienyloxy]-silane 
• 105426-90-2 {4-[(1-Ethoxy-ethoxy)-tributylstannanyl-methyl]-furan-2-yl}-trimethyl-silane 
• 105426-86-6 (2Z,6E)-3-Dimethoxymethyl-7-methyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6-dienoic acid tert-butyl ester 
• 105426-92-4 4-[(3Z,7E)-4-Dimethoxymethyl-1-(1-ethoxy-ethoxy)-8-methyl-10-(2,6,6-trimethyl-cyclohex-1-enyl)-deca-3,7-dienyl]-5-hydroxy-5H-furan-2-one 

Relevant articles and documents

Total synthesis of manoalide

Me3Al/AlCl3-mediated hetero-Diels-Alder (HDA) additions of 2-silyloxy-1,3-dienes to formylated butenolide 6 containing a protected hydroxy function afford, in one step, a variety of pyranofuranones including manoalide precursor 16, which is a stable monoprotected seco-manoalide.

Synthesis of manoalide using a 1,2-metallate rearrangement

Manoalide, a marine antiinflammatory sesterterpenoid, has been synthesised using a 1,2-metallate rearrangement of a higher order cuprate and a Pd0-catalysed carbonylation of an iodo alkene to generate the central dihydropyranone ring.

Two Syntheses of Manoalide via Heteroatom-Assisted Alkyne Carbometallation

Two approaches to the sesterterpenoid phospholipase A2 inhibitors seco-manoalide (3) and manoalide (1) are described based on carbometallation of propargylic alcohols to generate the functionalised C6-C7 trisubstituted alkene.Both syntheses also deploy the photooxidation of a furan in order to generate a 4-substituted 5-hydroxy-2(5H)-furanone moiety.

HIGHLY EFFICIENT TOTAL SYNTHESIS OF MANOALIDE AND SECO-MANOALIDE VIA Pd(0) CATALYZED COUPLING OF ALLYLHALIDE WITH CO AND 2-SILYL-4-STANNYLFURAN

Total synthesis of manoalide and seco-manoalide from an allylchloride derivative was achieved by 6 steps in 56.4percent overall yield by Pd(0) catalyzed coupling with CO and 2-trimethylsilyl-4-tributylstannylfuran followed by chemoselective oxidation of 2-trimethylsilylfuran with 1O2.

TOTAL SYNTHESIS OF MANOALIDE AND SECO-MANOALIDE

The first synthesis of manoalide and seco-manoalide from methyl 7,8-dihydro-β-ionylidene acetate was achieved in high yield by the new method utilizing regiospecific singlet oxigen oxidation of 3-alkenyl-5-trimethylsilylfuran to β-alkenyl-γ-hydroxybutenol