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Nerolic acid

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Nerolic acid
Names
Preferred IUPAC name (2Z)-3,7-Dimethylocta-2,6-dienoic acid
Other names Neric acid; 3,7-Dimethylocta-2,6-dienoic acid; 3,7-Dimethyl-2,6-octadienoic acid,
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
EC Number
  • 202-058-4
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H16O2/c1-8(2)5-4-6-9(3)7-10(11)12/h5,7H,4,6H2,1-3H3,(H,11,12)/b9-7+Key: ZHYZQXUYZJNEHD-VQHVLOKHSA-N
SMILES
  • CC(=CCC/C(=C/C(=O)O)/C)C
Properties
Chemical formula C10H16O2
Molar mass 168.236 g·mol
Related compounds
Related isomers Geranic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Nerolic acid, also known as (Z)-3,7-dimethyl-2,6-octadienoic acid, is an organically-derived chemical.

In nature

Nerolic acid is found in the Nasonov scent gland of honey-bees along with geraniol, geranic acid, citral, farnesol, and nerol. Of these, nerolic acid, geraniol, and farnesol are present in the highest proportions.

It is one of the five compounds that are part of the essential oils of Myrcia Ovata.

It is a compound also found in great quantity in Myrcia lundiana and it possess antifungal properties against pathogens such as Fusarium solani, and Lasiodiplodia theobromae. Both Myrcia Ovata and Myrcia lundiana are part of the Myrtaceae family plant, both containing a certain percentage of Nerolic acid compound.

In addition to this, Nerolic acid is also a principal chemical compound of essential oils of lemongrass, and is also believed to possess antifungal properties.

References

  1. Winston, Mark L (1987). The Biology of the Honey Bee. First Harvard University Press. p. 37. ISBN 978-0-674-07409-5.
  2. R Boch; DA Shearer (April 18, 1964). "Identification of Nerolic and Geranic Acids in the Nassanoff Pheromone of the Honey Bee". Nature. 202 (4929): 320–321. Bibcode:1964Natur.202..320B. doi:10.1038/202320a0. S2CID 4283000.
  3. Free JB, Ferguson AW, Picket JA (1981). "Evalutation of Various Components of the Nasonov Pheromone used by clustering honeybees". Physiological Entomology. 6 (3): 263–268. doi:10.1111/j.1365-3032.1981.tb00270.x. S2CID 86732208.
  4. ^ White, Larissa Alves Secundo; Blank, Arie Fitzgerald; Gagliardi, Paulo Roberto; Arrigoni-Blank, Maria de Fátima; Nizio, Daniela Aparecida de Castro; Sampaio, Taís Santos; Alves, Mércia Freita; Almeida-Pereira, Camila Santos (2019-10-15). "In vitro antifungal activity of Myrcia ovata essential oils and their major compounds against pathogens of citrus, sweet potato, and coconut". Bioscience Journal. 35 (6): 1696. doi:10.14393/BJ-v35n6a2019-42425. ISSN 1981-3163. S2CID 213523415.
  5. ^ Alves, Mércia Freitas; Nizio, Daniela Aparecida de Castro; Sampaio, Taís Santos; Nascimento, Alberto Ferreira do; Brito, Fabiany de Andrade; Melo, Juliana Oliveira de; Arrigoni-Blank, Maria de Fátima; Gagliardi, Paulo Roberto; Machado, Samisia Maria Fernandes; Blank, Arie Fitzgerald (2016-07-01). "Myrcia lundiana Kiaersk native populations have different essential oil composition and antifungal activity against Lasiodiplodia theobromae". Industrial Crops and Products. 85: 268. doi:10.1016/j.indcrop.2016.03.039. ISSN 0926-6690.
  6. Sargenti, S. R.; Lanças, F. M. (1997-09-01). "Supercritical fluid extraction ofCymbopogon citratus (DC.) Stapf". Chromatographia. 46 (5): 286. doi:10.1007/BF02496320. ISSN 1612-1112. S2CID 92933820.
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