Nerolic acid

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	4613-38-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	4472008;
EC Number	202-058-4;
PubChem CID	5275520;
UNII	6K8MFD7K03 ;
CompTox Dashboard (EPA)	DTXSID90109995 ;
	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−1
Related compounds
Related isomers	Geranic acid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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.^[1]^[2]^[3]

It is one of the five compounds that are part of the essential oils of Myrcia Ovata.^[4]

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.^[5] Both Myrcia Ovata and Myrcia lundiana are part of the Myrtaceae family plant, both containing a certain percentage of Nerolic acid compound.^[4]^[5]

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. ^[6]

References

^ Winston, Mark L (1987). The Biology of the Honey Bee. First Harvard University Press. p. 37. ISBN 978-0-674-07409-5.
^ 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.
^ 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.
^ ^a ^b 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.
^ ^a ^b 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.
^ 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.

[honeybeebiology-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.

[:0-4] 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.

[:1-5] 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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