Name: 4,7,10,13,16,19,22-Heptaoxapentacosa-1,24-diyne
Brand: BOC Sciences
Rating: 5 (1 reviews)

Size

Price

Stock

Quantity

$--

In stock

Purity

>95%

Solubility

Soluble in DMSO

Appearance

Pale Yellow or Colorless Oily Liquid

Storage

Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)

Shipping

Room temperature in continental US; may vary elsewhere.

IUPACName

3-[2-[2-[2-[2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]prop-1-yne

Synonyms

Bis-propargyl-PEG7; Bis propargyl-PEG6; Bis[2-[2-[2-(propargyloxy)ethoxy]ethoxy]ethyl] ether

Boiling Point

421.9±40.0 °C at 760 mmHg

Density

1.061±0.06 g/cm3 (Predicted)

InChI Key

WJGHENNJCGFCLO-UHFFFAOYSA-N

InChI

InChI=1S/C18H30O7/c1-3-5-19-7-9-21-11-13-23-15-17-25-18-16-24-14-12-22-10-8-20-6-4-2/h1-2H,5-18H2

SMILES

C#CCOCCOCCOCCOCCOCCOCCOCC#C

1. Biosynthesis of docosahexaenoic acid (DHA, 22:6-4, 7,10,13,16,19): two distinct pathways

Xiao Qiu Prostaglandins Leukot Essent Fatty Acids. 2003 Feb;68(2):181-6.doi: 10.1016/s0952-3278(02)00268-5.

Docosahexaenoic acid (DHA) has long been recognized for its beneficial effect in humans, but its biosynthetic pathway has not been clearly established until recently. According to Sprecher, in mammals, DHA is synthesized via a retro-conversion process in peroxisomes-the aerobic delta4 desaturation-independent pathway. Recent identification of a Thraustochytrium delta4 desaturase indicates that delta4 desaturation is indeed involved in DHA synthesis in Thraustochytrium. More interestingly, an alternative pathway for DHA biosynthesis-the anaerobic polyketide synthase pathway was also reported recently to occur in Schizochytrium, another member of the Thraustochytriidae. This mini-review attempts to assess the latest research on these distinct pathways for DHA biosynthesis.

2. Development of certified reference materials for four polyunsaturated fatty acid esters

Weizhu Chen, Wenhui Jin, Yiping Zhang, Hua Fang, Hui Chen, Zhuan Hong, Xiaoyan Huang Food Chem. 2022 Sep 30;389:133006.doi: 10.1016/j.foodchem.2022.133006.Epub 2022 Apr 20.

Certified reference materials (CRMs) with high accuracy and traceability are essential tools for the validation of analytical methods and calibration of equipment. In this study, purity CRMs for four polyunsaturated fatty acids (PUFAs) esters, namely, cis-(4,7,10,13,16,19)- Docosahexaenoic acid methyl ester (DHA-ME), cis-4,7,10,13,16,19- Docosahexaenoic acid ethyl ester (DHA-EE), cis-(5,8,11,14,17)- Eicosapentaenoic acid methyl ester (EPA-ME) and cis-(5,8,11,14,17)- Eicosapentaenoic acid ethyl ester (EPA-EE), were first developed according to the ISO Guide. The CRMs' purity values were assigned based on the average of quantitative nuclear magnetic resonance and mass balance approaches. The certified value with expanded uncertainties (k = 2, 95% confidence interval) were determined to be (98.8 ± 0.4) %, (99.0 ± 0.3) %, (98.9 ± 0.4) % and (98.9 ± 0.4) % for DHA-ME, DHA-EE, EPA-ME and EPA-EE, respectively. The four PUFAs esters were homogeneous and stable for 12 months at -4 °C and 7 days at 50 °C.

3. Effect of 4,7,10,13,16,19-docosahexaenoic acid on triglyceride accumulation and secretion in rat hepatocytes in culture

L J Martin, G B Reaidi, G R Gavino, V C Gavino Lipids. 1991 May;26(5):374-80.doi: 10.1007/BF02537202.

We have investigated the effect of oleic (18:1) and 4,7,10,13,16,19-docosahexaenoic (22:6 omega 3) acids on triglyceride (TG) accumulation, secretion and reuptake in rat hepatocytes in culture. We also calculated the percentage of total TG, TG-esterified 18:1 and TG-esterified 22:6 omega 3 that were secreted relative to the total accumulation (intra + extracellular TG). Both fatty acids were incorporated mainly in the intracellular TG fraction. Treatment with 18:1 but not with 22:6 omega 3 increased the quantity of TG secreted into the culture medium relative to controls. Treatment with 22:6 omega 3 caused a greater accumulation of intracellular TG than 18:1. This arises in part from the preferential retention of 22:6 omega 3-enriched TG by the hepatocytes. At 24 hr, there was no longer any difference in the net secretion of TG by 18:1 and 22:6 omega 3-treated cells, which may be a consequence of the reuptake of TG-esterified 18:1. There was no reuptake of TG-esterified 22:6 omega 3. We conclude that inhibition of hepatocyte TG synthesis is not obligatory for 22:6 omega 3-induced diminution of TG secretion.

4,7,10,13,16,19,22-Heptaoxapentacosa-1,24-diyne, provides a rigid, extended carbon–oxygen scaffold that can support controlled spatial presentation of two binding modules. Its conjugated alkyne motif and ether-rich backbone are advantageous for tuning linker length, conformational bias, and overall physicochemical behavior in targeted protein degradation constructs. The subsequent points describe its structural features and practical considerations for PROTAC assembly.

Structure: The linker comprises a long polyether framework featuring multiple ether linkages and terminal alkyne functionality. Its conjugated diyne segment introduces linear, rigid geometry, while the oxygen-rich chain increases polarity and hydrogen-bonding capacity. Overall, it presents a flexible-to-rigid hybrid scaffold with stable carbon–carbon and carbon–oxygen bonds.

Reactivity: Suitable PROTAC construction commonly relies on coupling strategies that preserve alkyne integrity, such as alkyne-compatible functionalization or orthogonal click-type conjugations using appropriately functionalized partners. In practice, reactions are typically performed under conditions that minimize alkyne oxidation and ether cleavage, using inert atmospheres when necessary. Base- or nucleophile-mediated steps should be chosen to avoid side reactions on polyether chains, and catalysts should be selected for chemoselectivity toward the targeted coupling handle.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C₁V₁ = C₂V₂