28290-90-6

Basic information

• Product Name: 2-Dodecenoic acid, ethyl ester, (2E)-
• Synonyms: 2-Dodecenoic acid, ethyl ester, (2E)-;ETHYLDODEC-2-ENOATE;ethyl (E)-2-dodecenoate
• CAS NO: 28290-90-6
• Molecular Formula: C₁₄H₂₆O₂
• Molecular Weight: 226.35
• Mol File: 28290-90-6.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 291.2°C at 760 mmHg
• Flash Point: 142.4°C
• Appearance: /
• Density: 0.881g/cm³
• Vapor Pressure: 0.00197mmHg at 25°C
• Refractive Index: 1.448
• CAS DataBase Reference: 2-Dodecenoic acid, ethyl ester, (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Dodecenoic acid, ethyl ester, (2E)-(28290-90-6)
• EPA Substance Registry System: 2-Dodecenoic acid, ethyl ester, (2E)-(28290-90-6)

Safety Data

• Hazardous Substances Data: 28290-90-6(Hazardous Substances Data)

Usage

Description

2-Dodecenoic acid, ethyl ester, (2E)is an organic compound that serves as an intermediate in the synthesis of various bioactive molecules. It is characterized by its chemical structure, which includes a double bond in the (2E)configuration, and is derived from the esterification of 2-Dodecenoic acid with ethanol.

Uses

Used in Pharmaceutical Industry:
2-Dodecenoic acid, ethyl ester, (2E)is used as an intermediate in the synthesis of bioactive compounds for pharmaceutical applications. Specifically, it plays a crucial role in the production of (4E, 8E)-Sphingadienine-C18-1-phosphate (S680680), an analogue of (4E, 14Z)-Sphingadienine-C18 (S680630). This sphingoid base is derived from sea cucumber cerebroside and has demonstrated potential cytotoxicity activity against human colon cancer cells, making it a valuable compound in the development of cancer treatments.

InChI:InChI=1/C14H26O2/c1-3-5-6-7-8-9-10-11-12-13-14(15)16-4-2/h12-13H,3-11H2,1-2H3/b13-12+

Upstream product

• 112-31-2 caprinaldehyde 
• 2425-25-4 O,O-diethyl s-carboethoxymethyl phosphorothioate 
• 105-36-2 ethyl bromoacetate 
• 1071-46-1 hydrogen ethyl malonate 
• 112-30-1 1-Decanol 
• 51148-67-5 10-undecen-1-yl p-toluenesulfonate 
• 112-38-9 10-undecenoic acid 
• 112-43-6 10-Undecen-1-ol 
• 821-95-4 1-undecene 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 1026993-51-0 3-acetoxy-1-ethoxy-1-dodecyne 
• 1530-45-6 (carbethoxymethyl)triphenylphosphonium bromide 
• 14402-93-8 dipentylzinc 

Downstream Products

• 28254-78-6 (3R)-(-)-3-Hydroxydodecanoic acid 
• 1387556-99-1 C₁₉H₃₁N₃O₄S 
• 1387556-98-0 (2S,3R)-2-azido-3-hydroxydodecyl 4-methylbenzenesulfonate 
• 107796-97-4 (2S,3S)-(3-nonyloxiran-2-yl)methanol 
• 32466-54-9 (E)-2-dodecenoic acid 
• 20407-84-5 2-dodecenal 
• 602275-71-8 (R)-4-[Benzyl-((R)-1-phenyl-ethyl)-amino]-1-trimethylsilanyl-2-trimethylsilanylmethyl-tridecan-2-ol 
• 602275-72-9 (4S,1'S)-4-(N-α-methylbenzyl-N'-benzylamino)-1-trimethylsilyl-2-(trimethylsilylmethyl)tridecan-2-ol 
• 556068-53-2 ethyl (3R)-3-{benzyl[(1R)-1-phenylethyl]amino}dodecanoate 
• 556068-55-4 (3S,1'S)-3-(N-α-methylbenzyl-N'-benzylamino)-dodecanoate 
• 22104-81-0 (2E)-dodec-2-en-1-ol 

Relevant articles and documents

Synthesis and evaluation of analogues of the glycinocin family of calcium-dependent antibiotics

The glycinocins are a class of calcium-dependent, acidic cyclolipopeptide antibiotics that are structurally related to the clinically approved antibiotic daptomycin. In this article, we describe the synthesis of a small library of glycinocin analogues that differ by variation in the exocyclic fatty acyl substituent. The glycinocin analogues were screened against a panel of Gram-positive bacteria (as well as Gram-negative P. aeruginosa). These analogues exhibited similar calcium-dependent activity to the parent natural products against Gram-positive bacteria but showed no activity against P. aeruginosa. The length of the fatty acid was shown to be important for optimal biological activity, while the hybridisation at the α,β position and branching within the fatty acyl chain had only subtle effects on activity.

Enantioselective total syntheses of (?)-clavaminol A and deacetyl (+)-clavaminol H

An efficient enantioselective approach to the syntheses of (?)-clavaminol A and deacetyl (+)-clavaminol H is presented, starting from n-decanol. The synthesis features Sharpless asymmetric dihydroxylation (AD), regioselective epoxide formation/opening and α-tosylation as key steps.

Total synthesis and in vitro bioevaluation of clavaminols A, C, H & deacetyl clavaminol H as potential chemotherapeutic and antibiofilm agents

A highly concise and expedient total synthesis of bioactive clavaminols (1-4) has been executed using commercially available achiral compound decanol. The synthetic strategy relied on trans-Wittig olefination, Sharpless asymmetric epoxidation, regioselective azidolysis and in situ detosylation followed by reduction as key reactions with good overall yield. Based on biological evaluation studies of all the synthesized compounds, it was observed that the clavaminol A (1) exhibited good cytotoxicity against DU145 and SKOV3 cell lines with IC50 value of 10.8 and 12.5 μM, respectively. Clavaminol A (1) and deacetyl clavaminol H (3) displayed selective promising inhibition towards Gram-positive pathogenic bacterial strains and showed good antifungal activity against the tested Candida strains. In addition, compounds 1 and 3 have demonstrated significant bactericidal activity. Compound 3 was found to be equipotent to the standard drug Miconazole displaying MFC value of 15.6 μg/mL against Candida albicans MTCC 854, C. albicans MTCC 1637, C. albicans MTCC 3958 and Candida glabrata MTCC 3019. Compounds 1 and 3 were also able to inhibit the biofilm formation of Micrococcus luteus MTCC 2470 and Staphylococcus aureus MLS16 MTCC 2940. Clavaminol A (1) increased the levels of reactive oxygen species (ROS) accumulation in M. luteus MTCC 2470.