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β-Cyclocitral

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(Redirected from Β-cyclocitral)
β-Cyclocitral
Names
IUPAC name
2,6,6-Trimethylcyclohexene-1-carbaldehyde
Other names
1-Formyl-2,6,6-trimethyl-1-cyclohexene
Identifiers
3D model (JSmol)
2042086
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.439 Edit this at Wikidata
EC Number
  • 207-081-3
UNII
  • InChI=1S/C10H16O/c1-8-5-4-6-10(2,3)9(8)7-11/h7H,4-6H2,1-3H3
    Key: MOQGCGNUWBPGTQ-UHFFFAOYSA-N
  • CC1=C(C(CCC1)(C)C)C=O
Properties
C10H16O
Molar mass 152.237 g·mol−1
Boiling point 62–63 °C (144–145 °F; 335–336 K)
86.14 mg/L
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H302, H312, H315, H319, H332, H335
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

β-Cyclocitral (beta-cyclocitral) is an apocarotenoid derived from the C7 oxidation of β-carotene. This apocarotenoid has revived interest due to its roles in plant development. β-cyclocitral has been found endogenously in a variety of organisms including plants, cyanobacteria, fungi and animals.[2] β-Cyclocitral is a volatile compound that contributes to the aroma of various fruits, vegetables and ornamental plants.[3] In plants, β-cyclocitral was found to be an important regulator in root development.[4]

Application

[edit]

β-Cyclocitral is used as an analytical standard for the determination of volatile organic compounds in saffron due to its analog structure to safranal.

Because β-cyclocitral is associated with cyanobacteria death, it is an analyte that can be tracked in bodies of water to monitor cyanobacteria blooms.[5]

It has also been found to promote the growth of roots in rice, prompting its consideration as a potential agricultural tool.[6]

Biosynthesis

[edit]

The biosynthesis of β-cyclocitral relies on the formation of β-carotene through the isoprenoid biosynthetic pathway underpinning carotenoid formation. Similar to other apocarotenoids, the formation of β-cyclocitral can occur via the enzymatic and non-enzymatic oxidative cleavage of double bonds in β-carotene.[7] For β-cyclocitral to form, the cleavage of C7-C8 double bonds are needed. While no enzyme has been identified to have high specificity for the production of β-cyclocitral, a carotenoid cleavage dioxygenase (CCD4) has been identified as being capable of cleaving β-carotene at the needed position.[8] 13-lipoxygenase (LOX2) has also been identified to cleave β-carotene at the C7 position.[9] β-cyclocitral can also be formed from the direct oxidation of β-carotene by reactive oxygen species, especially singlet oxygen (1O2). In plants, 1O2 is mainly produced from excited chlorophylls in the reaction center of PSII where β-carotene serves to quench the reactive oxygen species.[10]

Beta-Cyclocitral biosynthesis pathway
β-Cyclocitral biosynthesis

References

[edit]
  1. ^ "beta-Cyclocitral". pubchem.ncbi.nlm.nih.gov.
  2. ^ Havaux, Michel (October 2020). "β-Cyclocitral and derivatives: Emerging molecular signals serving multiple biological functions". Plant Physiology and Biochemistry. 155: 35–41. doi:10.1016/j.plaphy.2020.07.032. ISSN 0981-9428. PMID 32738580. S2CID 220925143.
  3. ^ Condurso, Concetta (October 2016). "Bioactive volatiles in Sicilian (South Italy) saffron: safranal and its related compounds". Journal of Essential Oil Research. 29 (3): 221–227. doi:10.1080/10412905.2016.1244115. S2CID 100505185.
  4. ^ Dickinson, Alexandra (May 2019). "β-Cyclocitral is a conserved root growth regulator". Proceedings of the National Academy of Sciences. 116 (21): 10563–10567. Bibcode:2019PNAS..11610563D. doi:10.1073/pnas.1821445116. PMC 6534974. PMID 31068462.
  5. ^ Huang, Heyong (2018). "Distributions of four taste and odor compounds in the sediment and overlying water at different ecology environment in Taihu Lake". Scientific Reports. 8 (8): 6179. Bibcode:2018NatSR...8.6179H. doi:10.1038/s41598-018-24564-z. PMC 5906450. PMID 29670292.
  6. ^ Keeley, Jim. "A Plant Hormone that Speeds Root Growth Could Be a New Agricultural Tool". Howard Hughhes Medical Institute. Retrieved 6 June 2023.
  7. ^ Havaux, Michel (2020). "β-Cyclocitral and derivatives: Emerging molecular signals serving multiple biological functions". Plant Physiology and Biochemistry. 155: 35–41. doi:10.1016/j.plaphy.2020.07.032. PMID 32738580. S2CID 220925143.
  8. ^ Maria, Rodrigo (2013). "A novel carotenoid cleavage activity involved in the biosynthesis of Citrus fruit-specific apocarotenoid pigments". Journal of Experimental Botany. 64 (14): 4461–4478. doi:10.1093/jxb/ert260. PMC 3808326. PMID 24006419.
  9. ^ Gao, Lei (2019). "The tomato pan-genome uncovers new genes and a rare allele regulating fruit flavor". Nature Genetics. 51 (6): 1044–1051. doi:10.1038/s41588-019-0410-2. PMID 31086351. S2CID 256819279.
  10. ^ Triantaphylidès, Christian (2009). "Singlet oxygen in plants: production, detoxification and signaling". Trends in Plant Science. 14 (4): 219–228. doi:10.1016/j.tplants.2009.01.008. PMID 19303348.