16900-60-0

Basic information

• Product Name: 11-dodecynoic acid
• Synonyms: 11-dodecynoic acid
• CAS NO: 16900-60-0
• Molecular Formula: C12H20 O2
• Molecular Weight: 196.29
• Mol File: 16900-60-0.mol

Chemical Properties

• Melting Point: 48°C (estimate)
• Boiling Point: 356.18°C (rough estimate)
• Flash Point: 149.8°C
• Appearance: /
• Density: 0.9746 (rough estimate)
• Vapor Pressure: 0.000137mmHg at 25°C
• Refractive Index: 1.4096 (estimate)
• CAS DataBase Reference: 11-dodecynoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 11-dodecynoic acid(16900-60-0)
• EPA Substance Registry System: 11-dodecynoic acid(16900-60-0)

Safety Data

• Hazardous Substances Data: 16900-60-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
11-Dodecynoic acid is used as a versatile building block in organic synthesis for the creation of compounds with unique functional properties. Its terminal alkyne group allows for a variety of chemical reactions, making it a valuable component in the synthesis of specialty chemicals and pharmaceuticals.
Used in Material Science:
In material science, 11-Dodecynoic acid is utilized for its potential to contribute to the development of novel materials with specific properties. Its incorporation into polymers and other materials can enhance their characteristics, such as strength, flexibility, or chemical resistance.
Used in Medicinal Chemistry:
11-Dodecynoic acid is used as a compound of interest in medicinal chemistry due to its potential biological activities. Its antimicrobial properties make it a candidate for the development of new antibiotics, while its antitumor properties suggest it could be used in the creation of anticancer drugs.
Used in Antimicrobial Applications:
11-Dodecynoic acid is employed as an antimicrobial agent, effective against a range of bacteria. Its unique structure allows it to disrupt bacterial cell membranes or interfere with essential cellular processes, providing a new avenue for combating antibiotic-resistant strains.
Used in Antitumor Applications:
In the realm of antitumor research, 11-Dodecynoic acid is studied for its potential to inhibit tumor growth and proliferation. Its incorporation into drug development pipelines could lead to the discovery of new therapeutic agents for the treatment of various types of cancer.
Used in Pharmaceutical Development:
11-Dodecynoic acid is used in pharmaceutical development as a precursor or intermediate in the synthesis of drugs with specific therapeutic targets. Its unique chemical properties can be leveraged to create molecules with improved efficacy, selectivity, or reduced side effects.

InChI:InChI=1/C12H20O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h1H,3-11H2,(H,13,14)

Upstream product

• 53163-99-8 11-oxoundecanoic acid 
• 21047-57-4 diethyl (1-diazo-2-oxopropyl)phosphonate 
• 2777-65-3 undec-10-ynoic acid 
• 7766-50-9 1-undecen-11-ylbromide 
• 50530-12-6 10-bromodecanoic acid 
• 95386-96-2 Acetic acid 11-cyano-undecyl ester 
• 73782-16-8 12-hydroxydodecanoic nitrile 
• 5810-18-4 11-cyanoundecanoic acid 
• 35042-91-2 11-cyanoundecanoyl chloride 
• 65423-25-8 11-dodecenoic acid 
• 5048-44-2 11-dodecenenittrile 
• 947-05-7 oxacyclotridecan-2-one 
• 108545-36-4 12-(2-Nitro-phenylselanyl)-dodecanoic acid methyl ester 
• 26825-95-6 methyl 12-bromododecanoate 

Downstream Products

• 19220-40-7 11-octadecynoic acid 
• 1351669-55-0 (S)-((1S,2R)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) 2-((S)-3-(3,4-dimethoxyphenyl)-1-hydroxypropyl)dodec-11-ynoate 
• 1351669-57-2 (S)-((1S,2R)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) 2-((S)-1-5-(3-dimethylaminopropylsulfonyl)-1-hydroxypentyl)dodec-11-ynoate 
• 1351669-60-7 (S)-2-((S)-3-(3,4-dimethoxyphenyl)-1-hydroxypropyl)dodec-11-ynoic acid 
• 1351669-43-6 (3S,4S)-3-(dec-9-ynyl)-4-(3,4-dimethoxyphenetyl)oxetan-2-one 
• 1351669-61-8 (S)-methyl 2-((S)-3-(3,4-dimethoxyphenyl)-1-hydroxypropyl)dodec-11-ynoate 
• 2450-31-9 1,24-tetracosanedi acid 
• 77159-57-0 15-hydroxy-11Z,13E-eicosadienoic acid 
• 24567-43-9 11-dodecynoic acid methyl ester 

Relevant articles and documents

On the synthesis of vinyl isonitriles

A reversal of the stereochemistry of base mediated isomerisation of some isonitrile epoxides to hydroxy-vinyl isonitriles on changing from lithium diisopropylamide to lithium bis(trimethylsilyl)amide is reported and applied to a synthesis of racemic desepoxyaerocyanidin.

INSULIN CONJUGATES

The present invention relates to a conjugate comprising a sulfonamide of formula (I) and an active pharmaceutical ingredient such as an insulin analog comprising at least one mutation relative to the parent insulin, wherein the insulin analog comprises a mutation at position B16 which is substituted with a hydrophobic amino acid and/or a mutation at position B25 which is substituted with a hydrophobic amino acid. The present invention further relates to a sulfonamide of formula (A). Moreover, the present invention relates to an insulin analog comprising at least one mutation relative to the parent insulin.

A Sequential Homologation of Alkynes and Aldehydes for Chain Elongation with Optional 13C-Labeling

Terminal alkynes (RCCH) are homologated by a sequence of ruthenium-catalyzed anti-Markovnikov hydration of alkyne to aldehyde (RCH2CHO), followed by Bestmann-Ohira alkynylation of aldehyde to chain-elongated alkyne (RCH2CCH). Inverting the sequence by starting from aldehyde brings about the reciprocal homologation of aldehydes instead. The use of 13C-labeled Bestmann-Ohira reagent (dimethyl ((1-13C)-1-diazo-2-oxopropyl)phosphonate) for alkynylation provides straightforward access to singly or, through additional homologation, multiply 13C-labeled alkynes. The labeled alkynes serve as synthetic platform for accessing a multitude of specifically 13C-labeled products. Terminal alkynes with one or two 13C-labels in the alkyne unit have been submitted to alkyne-azide click reactions; the copper-catalyzed version (CuAAC) was found to display a regioselectivity of >50 000:1 for the 1,4- over the 1,5-triazine isomer, as shown analytically by 13C NMR spectroscopy.

Structural Analysis and Inclusion Mechanism of Native and Permethylated α-Cyclodextrin-Based Rotaxanes Containing Alkylene Axles

Native α-cyclodextrin- (α-CD) and permethylated α-CD (PMeCD)-based rotaxanes with various short alkylene chains as axles can be synthesized through a urea end-capping method. Native α-CD tends to form [3]- or [5]pseudorotaxanes and not [2]- or [4]pseudorotaxanes, which indicates that the coupled CDs act as a single fragment. End-capping reactions of the pseudorotaxanes with C18 and C24 axle lengths do not occur because the axle termini are covered by the densely stacked CDs. The number of PMeCDs on the pseudorotaxane is flexible and mainly depends on the axle length. Peracetylated α-CD (PAcCD)-based rotaxanes are synthesized through O-acetylation of the α-CD-based rotaxanes without any decomposition of the rotaxanated structures. The structures of PMeCD-based [3]- and [4]rotaxanes, and the molecular dynamics calculations on [3]pseudorotaxanes, indicate that the tail face of PMeCDs is regularly directed toward the axle termini. On the basis of the results obtained, it can be concluded that the directions and numbers of CDs in rotaxanes containing short alkylene chains depend on 1)the interactions between CDs, 2)the length of the alkylene axle, and 3)the interactions between the axle end and tail face of the CD. Come on in! Native and permethylated α-cyclodextrin (CD)-based rotaxanes with various short alkylene axles are synthesized with a urea end-capping method. The directions and number of the CD wheels depend on the interactions between CDs, the axle length, and the interactions between axle ends and the tail face of the CDs (see figure).

Identification of acyl protein thioesterases 1 and 2 as the cellular targets of the ras-signaling modulators palmostatin B and M

Finding the target: Activity-based proteomic profiling probes based on the depalmitoylation inhibitors palmostatin B and M (see picture) have been synthesized and were found to target acyl protein thioesterase 1 (APT1) and 2 (APT2) in cells. Copyright

17(R),18(S)-Epoxyeicosatetraenoic acid, a potent eicosapentaenoic acid (EPA) derived regulator of cardiomyocyte contraction: Structure-activity relationships and stable analogues

17(R),18(S)-Epoxyeicosatetraenoic acid [17(R),18(S)-EETeTr], a cytochrome P450 epoxygenase metabolite of eicosapentaenoic acid (EPA), exerts negative chronotropic effects and protects neonatal rat cardiomyocytes against Ca 2+-overload with EC50 ≈ 1-2 nM. Structure-activity studies revealed that a cis-Δ11,12- or Δ14,15- olefin and a 17(R),18(S)-epoxide are minimal structural elements for antiarrhythmic activity whereas antagonist activity was often associated with the combination of a Δ14,15-olefin and a 17(S),18(R)-epoxide. Compared with natural material, the agonist and antagonist analogues are chemically and metabolically more robust and several show promise as templates for future development of clinical candidates.

DIYNE COMPOSITIONS

A novel class of diyne compounds and diyne salts provided herein are effective and potent Olel protein inhibitors, useful for treating fungal pathogens. Compounds, fungicides and methods are provided as novel, potent and broad spectrum antifungal agents for treatment against a wide variety of fungal pathogens in humans and animals, and in the agricultural setting.

Novel eicosanoid derivatives

The present invention provides compounds (n-3 PUFA derivatives) of formula (I): that modulate conditions associated with cardiac damage, especially cardiac arrhythmias.

14,15-Epoxyeicosa-5,8,11-trienoic acid (14,15-EET) surrogates containing epoxide bioisosteres: Influence upon vascular relaxation and soluble epoxide hydrolase inhibition

All-cis-14,15-epoxyeicosa-5,8,11-trienoic acid (14,15-EET) is a labile, vasodilatory eicosanoid generated from arachidonic acid by cytochrome P450 epoxygenases. A series of robust, partially saturated analogues containing epoxide bioisosteres were synthesized and evaluated for relaxation of precontracted bovine coronary artery rings and for in vitro inhibition of soluble epoxide hydrolase (sEH). Depending upon the bioisostere and its position along the carbon chain, varying levels of vascular relaxation and/or sEH inhibition were observed. For example, oxamide 16 and N-iPr-amide 20 were comparable (ED50 1.7 μM) to 14,15-EET as vasorelaxants but were approximately 10-35 times less potent as sEH inhibitors (IC50 59 and 19 μM, respectively); unsubstituted urea 12 showed useful activity in both assays (ED50 3.5 μM, IC50 16 nM). These data reveal differential structural parameters for the two pharmacophores that could assist the development of potent and specific in vivo drug candidates.

Synthesis of carboxyl-tethered symmetric conjugated polyenes as fluorescent transmembrane probes of lipid bilayers

The synthesis of a new series of fluorescent transmembrane probes in which two hydrophilic methyl ester or carboxyl groups are connected by a polymethylene chain, with four, five or six conjugated double bonds in a central position, is reported. The length of the linear structures was designed to match the width of typical lipid bilayers. These bolaamphiphilic compounds result, with overall yields higher than 80%, from an easy PdII-catalyzed double cross-coupling between terminal acetylene esters and conjugated 1,ω-dihalopolyenes, followed by selective triple bond partial reduction with activated zinc, and iodine isomerization to the all-(E) isomer. An alternative approach, based on a Stille double cross-coupling between the appropriate all-(E)-ω-halopolyenes and (E)-bis(tributylstannyl)ethene, yielded mixtures that could not be resolved by standard chromatographic methods due to the presence of other simultaneous coupling reactions, which are also discussed in detail. Nevertheless, the Stille method can be of utility for the obtention of carbonyl-polyene conjugated analogs. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.