23986-74-5 Usage
Description
Germacrene D, also known as 1-methyl-5-methylene-8-(1-methylethyl)-1,6-cyclodecadiene, is a naturally occurring sesquiterpene found in various plants. It is characterized by its unique chemical structure, which contributes to its distinct properties and applications. Germacrene D is known for its insect-repellent properties and is used in the design of analogs of olfactory ligands.
Uses
Used in Insect Repellent Applications:
Germacrene D is used as a plant-derived insect repellent, particularly effective against a variety of insects. Its natural origin and repellent properties make it a preferred choice for eco-friendly pest control solutions.
Used in Fragrance and Flavor Industry:
Germacrene D is used as a key component in the synthesis of various fragrances and flavors due to its unique olfactory properties. It contributes to the development of new and innovative scents for the perfume and food industries.
Used in Essential Oil Extraction:
Germacrene D is present in the extraction of essential oils from plants, where it plays a significant role in the overall aroma and therapeutic properties of the oil. It is often found in essential oils used for aromatherapy and in the production of natural products for various applications.
Used in Pharmaceutical Research:
Due to its unique chemical structure and biological activity, germacrene D is also used in pharmaceutical research as a potential lead compound for the development of new drugs, particularly in the areas of insect repellency and olfactory research.
Check Digit Verification of cas no
The CAS Registry Mumber 23986-74-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,3,9,8 and 6 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 23986-74:
(7*2)+(6*3)+(5*9)+(4*8)+(3*6)+(2*7)+(1*4)=145
145 % 10 = 5
So 23986-74-5 is a valid CAS Registry Number.
InChI:InChI=1/C15H24/c1-12(2)15-10-8-13(3)6-5-7-14(4)9-11-15/h7-8,10,12,15H,3,5-6,9,11H2,1-2,4H3/b10-8+,14-7+/t15-/m0/s1
23986-74-5Relevant articles and documents
Mechanism and Stereochemistry of the Germacradienol/Germacrene D Synthase of Streptomyces coelicolor A3(2)
He, Xiaofei,Cane, David E.
, p. 2678 - 2679 (2004)
Incubation of farnesyl diphosphate (1, FPP) with recombinant germacradienol synthase from Streptomyces coelicolor A3(2) gave, in addition to (4S,7R)-germacra-1(10)E,5E-diene-11-ol (2), 15% of (?)-germacrene D (5). Incubations of [1,1-2HM2]FPP (1a), (1R)-[1-2H]FPP (1b), and (1S)-[1-2H]FPP (1c) with germacradienol/germacrene D synthase and analysis of the resulting samples of germacradienol (2) and germacrene D (5) by a combination of 1H, 2H, and 13C NMR and mass spectrometry established that it is H-1si of FPP that is lost in the formation of germacradienol (2) and that undergoes 1,3-hydride transfer in the formation of (?)-germacrene D (5). The proportion of the two products was also sensitive to isotopic labeling, with cyclization of (1S)-[1-2H]FPP (1c) giving an increased proportion (35%) of 5. These results could be explained by a mechanism involving partitioning of a common helminthogermacradienyl cation intermediate 7. Copyright
Chemoenzymatic preparation of germacrene analogues
Cascon, Oscar,Touchet, Sabrina,Miller, David J.,Gonzalez, Veronica,Faraldos, Juan A.,Allemann, Rudolf K.
, p. 9702 - 9704 (2012)
A small library of novel germacrenes was generated using a combination of two plant enzymes, germacrene A synthase, and D synthase and modified farnesyl diphosphate (FDP) analogues. This chemoenzymatic approach allows the preparation of potentially valuable volatiles for biological studies. The Royal Society of Chemistry 2012.
OLFACTORY LIGANDS
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Paragraph 0109; 0111; 0113-0117, (2018/10/19)
The invention provides analogues of (S)-germacrene D analogue which have improved insect repellent properties compared to (S)-germacrene D analogue or which have insect attractant properties.