15575-14-1

Basic information

• Product Name: UNDECAPRENOL FROM AILANTHUS ALTISSIMA
• Synonyms: UNDECAPRENOL FROM AILANTHUS ALTISSIMA;3,7,11,15,19,23,27,31,35,39,43-Undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecen-1-ol;Betulaprenol-11
• CAS NO: 15575-14-1
• Molecular Formula: C₅₅H₉₀O
• Molecular Weight: 767.315
• Mol File: 15575-14-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 777°Cat760mmHg
• Flash Point: 114.9°C
• Appearance: /
• Density: 0.89g/cm³
• Vapor Pressure: 6.93E-28mmHg at 25°C
• Refractive Index: 1.509
• Storage Temp.: −20°C
• PKA: 14.69±0.10(Predicted)
• CAS DataBase Reference: UNDECAPRENOL FROM AILANTHUS ALTISSIMA(CAS DataBase Reference)
• NIST Chemistry Reference: UNDECAPRENOL FROM AILANTHUS ALTISSIMA(15575-14-1)
• EPA Substance Registry System: UNDECAPRENOL FROM AILANTHUS ALTISSIMA(15575-14-1)

Safety Data

• Hazard Codes: T
• Statements: 45-46-20/21/22-36/37/38
• Safety Statements: 53-23-26-36/37/39-45
• Hazardous Substances Data: 15575-14-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C55H90O/c1-45(2)23-13-24-46(3)25-14-26-47(4)27-15-28-48(5)29-16-30-49(6)31-17-32-50(7)33-18-34-51(8)35-19-36-52(9)37-20-38-53(10)39-21-40-54(11)41-22-42-55(12)43-44-56/h23,25,27,29,31,33,35,37,39,41,43,56H,13-22,24,26,28,30,32,34,36,38,40,42,44H2,1-12H3/b46-25+,47-27+,48-29+,49-31+,50-33+,51-35+,52-37+,53-39+,54-41+,55-43+

Upstream product

• 19427-26-0 ficaprenyl (α-D-glucopyranosyl phosphate) 
• 1186313-59-6 1-((2Z,6Z,10Z,14Z,18Z,22Z,26Z,30E,34E,38E)-1-benzyloxy-17-tosyl-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-9-yl)sulfonyl-4-methylbenzene 

Downstream Products

• 50880-97-2 GlcNAc-pyrophosphorylundecaprenol 
• 65592-99-6 Moraprenyl phosphate 
• 111729-63-6 4-phenylsulfonyl-3,7,11,15,19,23,27,31,35,39,43,47-dodecamethyloctatetraconta-2E,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E,38E,42E,46-dodecaen-1-ol 

Relevant articles and documents

From plant to probe: Semi-synthesis of labelled undecaprenol analogues allows rapid access to probes for antibiotic targets

Undecaprenol-containing glycolipids (UCGs) are essential precursors of bacterial glycopolymers and glycoproteins. We report a novel semi-synthetic strategy to prepare labelled UCGs directly from undecaprenol. This one-size-fits-all approach offers a concise and efficient method for obtaining labelled-UCGs, which will allow new mechanistic studies and inhibitor screens to be performed on novel antibiotic targets.

BIOSYNTHESIS OF A D-GLUCOSYL POLYISOPRENYL DIPHOSPHATE IN PARTICULATE PREPARATIONS OF MICROCOCCUS LYSODEIKTICUS

Particulate fractions of Micrococcus lysodeikticus incubated with UDP-D-glucose incorporated radioactivity into a chloroform-methanol-soluble, low-mol. wt. compound, and into a polymer.The low-mol. wt. compound consisted of a glucolipid that was extremely labile to mild acid hydrolysis with the formation of D-glucose, and to mild alkali, yielding 14C-labeled α-D-glucopyranose 1,2-phosphate and D-glucose 2-phosphate.The labeled glucolipid was eluted from a DEAE-cellulose column at a salt concentration higher than that required by synthetic ficaprenyl (D-glucopyranosyl phosphate), and it migrated more slowly than the latter compound in t.l.c.Formation of glucolipid was stimulated by exogenous ficaprenyl phosphate, but not by C55-dolichyl phophate.These results suggest that the glucolipid has the characteristic properties of a polyisoprenyl glucosyl diphosphate.