β-Cyclocitral is a volatile oxidized analogue of β-carotene and is a predator defense signal unique to Microcystis. β-Cyclocitral is one of the major volatile terpenoids that can upregulate the expression of defense genes, thereby enhancing adaptation to excess light (EL). Beta-Cyclocitral is a potent insect repellent.

Physicochemical Properties

Molecular Formula	C10H16O
Molecular Weight	152.23
Exact Mass	152.12
CAS #	432-25-7
PubChem CID	9895
Appearance	Typically exists as solid at room temperature
Density	0.947g/cm3
Boiling Point	212.1ºC at 760mmHg
Melting Point	62-63ºC
Flash Point	76.9ºC
Vapour Pressure	0.176mmHg at 25°C
Index of Refraction	n20/D 1.497(lit.)
LogP	2.711
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	1
Heavy Atom Count	11
Complexity	199
Defined Atom Stereocenter Count	0
SMILES	CC1=C(C=O)C(C)(C)CCC1
InChi Key	MOQGCGNUWBPGTQ-UHFFFAOYSA-N
InChi Code	InChI=1S/C10H16O/c1-8-5-4-6-10(2,3)9(8)7-11/h7H,4-6H2,1-3H3
Chemical Name	2,6,6-trimethylcyclohexene-1-carbaldehyde
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	β-Cyclocitral is a byproduct of the catalytic degradation of β-carotene, and research suggests that all species of the cyanobacterium Microcystis activate a particular carotene oxygenase to create it. The behavior of grazers is influenced by β-cyclocitral.
References	[1]. Alexandra J Dickinson, et al. β-Cyclocitral Is a Conserved Root Growth Regulator. Proc Natl Acad Sci U S A. 2019 May 21;116(21):10563-10567. [2]. Feifei Lv, et al. β-Cyclocitral Upregulates Salicylic Acid Signalling to Enhance Excess Light Acclimation in Arabidopsis. J Exp Bot. 2015 Aug;66(15):4719-32. [3]. Friedrich Jüttner, et al. β-Cyclocitral, a Grazer Defence Signal Unique to the Cyanobacterium Microcystis. J Chem Ecol. 2010 Dec;36(12):1387-97.
Additional Infomation	Beta-cyclocitral is a monoterpenoid formally derived from citral by cyclisation. It is a volatile compound produced by a cyanobacteria. It has a role as a bacterial metabolite. beta-Cyclocitral has been reported in Camellia sinensis, Zingiber mioga, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

DMSO: 100 mg/mL (656.86 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (16.42 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (16.42 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 3: ≥ 2.38 mg/mL (15.63 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 23.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	6.5690 mL	32.8450 mL	65.6901 mL
	5 mM	1.3138 mL	6.5690 mL	13.1380 mL
	10 mM	0.6569 mL	3.2845 mL	6.5690 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.