24738-51-0 Usage
Description
DODECA-2(E),4(E)-DIENOIC ACID ISOBUTYLAMIDE(P), also known as Dienamide A2, is an analog of the natural amides found in Echinacea species and Piper sarmentosum. It represents a new class of cannabinomimetic compounds that modulate TNFα mRNA expression in human monocytes/macrophages via the CB2 receptor. DODECA-2(E),4(E)-DIENOIC ACID ISOBUTYLAMIDE(P) exhibits unique binding affinities to cannabinoid receptors, with greater affinity than endogenous cannabinoids, and has the potential to be used in various applications due to its biological activities.
Uses
Used in Pharmaceutical Industry:
DODECA-2(E),4(E)-DIENOIC ACID ISOBUTYLAMIDE(P) is used as a cannabinomimetic compound for its ability to modulate TNFα mRNA expression in human monocytes/macrophages via the CB2 receptor. This makes it a potential candidate for the development of new drugs targeting inflammatory and immune-related disorders.
Used in Research Applications:
In research settings, DODECA-2(E),4(E)-DIENOIC ACID ISOBUTYLAMIDE(P) is used as a tool compound to study the effects and mechanisms of action of CB2 receptor activation. This helps researchers to better understand the role of the CB2 receptor in various physiological and pathological processes, potentially leading to the discovery of new therapeutic targets.
Used in Natural Pesticide Development:
As Kalecide is a natural pesticide derived from Echinacea angustifolia, Echinacea atrorubens, and Piper sarmentosum, DODECA-2(E),4(E)-DIENOIC ACID ISOBUTYLAMIDE(P) can be used as a lead compound in the development of new natural pesticides with potential applications in agriculture and horticulture for pest control and plant protection.
References
1) Gertsch?et al. (2004), Echinacea alkylamides modulate TNF-alpha gene expression via cannabinoid receptor CB2 and multiple signal transduction pathways; FEBS Lett., 577?563
2) Raduner?et al. (2006), Alkylamides from Echinacea are a new class of cannabinomimetics.? Cannabinoid type 2 receptor-dependent and -independent immunomodulatory effects; J. Biol. Chem., 281?14192
Check Digit Verification of cas no
The CAS Registry Mumber 24738-51-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,4,7,3 and 8 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 24738-51:
(7*2)+(6*4)+(5*7)+(4*3)+(3*8)+(2*5)+(1*1)=120
120 % 10 = 0
So 24738-51-0 is a valid CAS Registry Number.
InChI:InChI=1/C16H29NO/c1-4-5-6-7-8-9-10-11-12-13-16(18)17-14-15(2)3/h10-13,15H,4-9,14H2,1-3H3,(H,17,18)/b11-10+,13-12+
24738-51-0Relevant articles and documents
ALKAMIDE COMPOUNDS AND USES THEREOF
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, (2019/04/27)
The present disclosure relates to alkamide compounds and compositions for treating allergic diseases, pain, or itch.
DODECA-2E,4E-DIENE AMIDES AND THEIR USE AS MEDICAMENTS AND COSMETICS
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Paragraph 0082; 0091, (2015/11/16)
The present invention relates to a novel class of compounds, namely dodeca-2E, 4E-diem amides and their use a medicament, preferably as a dermatologic agent, and as a cosmetic:. These novel compounds are particularly useful in treating and/or preventing inflammation, irritation, itching, pruritus, pain, oedema and/or pro-allergic or allergic conditions in a patient. Usually they are topically applied to the skin or mucosa in the form of a pharmaceutical or cosmetic composition comprising the compound and a pharmaceutically and/or cosmetically acceptable carrier.
Bioavailability of echinacea constituents: Caco-2 monolayers and pharmacokinetics of the alkylamides and caffeic acid conjugates
Matthias, Anita,Penman, Kerry G.,Matovic, Nick J.,Bone, Kerry M.,De Voss, James J.,Lehmann, Reg P.
, p. 1242 - 1251 (2007/10/03)
Many studies have been done over the years to assess the effectiveness of Echinacea as an immunomodulator. We have assessed the potential bioavailability of alkylamides and caffeic acid conjugates using Caco-2 monolayers and compared it to their actual bioavailability in a Phase I clinical trial. The caffeic acid conjugates permeated poorly through the Caco-2 monolayers. Alkylamides were found to diffuse rapidly through Caco-2 monolayers. Differences in diffusion rates for each alkylamide correlated to structural variations, with saturation and N-terminal methylation contributing to decreases in diffusion rates. Alkylamide diffusion is not affected by the presence of other constituents and the results for a synthetic alkylamide were in line with those for alkylamides found in an ethanolic Echinacea preparation. We examined plasma from healthy volunteers for 12 hours after ingestion of Echinacea tablets manufactured from an ethanolic liquid extract. Caffeic acid conjugates could not be identified in any plasma sample at any time after tablet ingestion. Alkylamides were detected in plasma 20 minutes after tablet ingestion and for each alkylamide, pharmacokinetic profiles were devised. The data are consistent with the dosing regimen of one tablet three times daily and supports their usage as the primary markers for quality Echinacea preparations.
