Verbenone
(Synonyms: 马鞭草酮; (-)-Verbenone) 目录号 : GC61423
(-)-Verbenone (2-Pinen-4-one), an important component of the essential oil from rosemary, is an insect pheromone with a spicy odor and camphoraceous fragrance.
Cas No.:1196-01-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
(-)-Verbenone (2-Pinen-4-one), an important component of the essential oil from rosemary, is an insect pheromone with a spicy odor and camphoraceous fragrance.
| Cas No. | 1196-01-6 | SDF | |
| 别名 | 马鞭草酮; (-)-Verbenone | ||
| Canonical SMILES | O=C1[C@](C2)([H])C(C)(C)[C@]2([H])C(C)=C1 | ||
| 分子式 | C10H14O | 分子量 | 150.22 |
| 溶解度 | DMSO: 100 mg/mL (665.69 mM) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 6.6569 mL | 33.2845 mL | 66.569 mL |
| 5 mM | 1.3314 mL | 6.6569 mL | 13.3138 mL |
| 10 mM | 0.6657 mL | 3.3285 mL | 6.6569 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Verbenone Inhibits Attraction of Ips pini (Coleoptera: Curculionidae) to Pheromone-Baited Traps in Northern Arizona
J Econ Entomol 2020 Dec 9;113(6):3017-3020.PMID:32885233DOI:10.1093/jee/toaa192.
Recent outbreaks of engraver beetles, Ips spp. De Geer (Coleoptera: Curculionidae; Scolytinae), in ponderosa pine, Pinus ponderosa var. scopulorum Engelm. (Pinales: Pinaceae), forests of northern Arizona have resulted in widespread tree mortality. Current treatment options, such as spraying individual P. ponderosa with insecticides or deep watering of P. ponderosa in urban and periurban settings, are limited in applicability and scale. Thinning stands to increase tree vigor is also recommended, but appropriate timing is crucial. Antiaggregation pheromones, widely used to protect high-value trees or areas against attacks by several species of Dendroctonus Erichson (Coleoptera: Curculionidae; Scolytinae), would provide a feasible alternative with less environmental impacts than current treatments. We evaluated the efficacy of the antiaggregation pheromone Verbenone (4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one) in reducing attraction of pine engraver, I. pini (Say), to funnel traps baited with their aggregation pheromone in two trapping assays. Treatments included 1) unbaited control, 2) aggregation pheromone (bait), 3) bait with Verbenone deployed from a pouch, and 4) bait with Verbenone deployed from a flowable and biodegradable formulation (SPLAT Verb, ISCA Technologies Inc., Riverside, CA). Unbaited traps caught no beetles. In both assays, baited traps caught significantly more I. pini than traps with either formulation of Verbenone, and no significant difference was observed between the Verbenone pouch and SPLAT Verb. In the second assay, we also examined responses of Temnochila chlorodia (Mannerheim) (Coleoptera: Trogositidae), a common bark beetle predator. Traps containing Verbenone pouches caught significantly fewer T. chlorodia than the baited control and SPLAT Verb treatments. We conclude that Verbenone shows promise for reducing tree mortality from I. pini.
Comparisons of Efficiency of Two Formulations of Verbenone (4, 6, 6-trimethylbicyclo [3.1.1] hept-3-en-2-one) for Protecting Whitebark Pine, Pinus albicaulis (Pinales: Pinaceae) From Mountain Pine Beetle (Colopetera: Curculionidae)
J Econ Entomol 2021 Feb 9;114(1):209-214.PMID:33558908DOI:10.1093/jee/toaa289.
Whitebark pine, Pinus albicaulis Engelm., is a subalpine tree endemic to western North America. This species provides multiple ecosystem services and is suffering widespread mortality from mountain pine beetle, Dendroctonus ponderosae Hopkins. Verbenone is a pheromone produced as D. ponderosae feed, and high air concentrations of Verbenone deter D. ponderosae from colonizing trees. Synthetic Verbenone has been formulated into products used to prevent D. ponderosae from colonizing trees. We compared the ability of Verbenone pouches and SPLAT Verb to protect individuals and small stands of P. albicaulis. With individual trees in Montana, all treated trees survived regardless of Verbenone formulation and rate, whereas untreated trees suffered 70 and 90% mortality in 2015 and 2016. In plot experiments in California from 2015 to 2017, and Oregon from 2015 to 2018, Verbenone was applied to trees spaced ~10 m apart, and survival of small (12.7-23 cm DBH = diameter at 1.37 m height), medium (23.1-33 cm DBH) and large (>33 cm DBH) trees was compared. In California, where >80% of untreated trees survived, pouches increased survival ~2 to 3% and SPLAT Verb increased survival ~4 to 7% regardless of tree size. In Oregon, Verbenone pouches and SPLAT Verb performed similarly on medium and small trees, but large trees had greater survival when treated with SPLAT Verb (~93%) than pouches (~82%). Compared to Verbenone pouches, SPLAT Verb appears to better protect P. albicaulis from D. ponderosae.
Comparison by Life-Cycle Assessment of Alternative Processes for Carvone and Verbenone Production
Molecules 2022 Aug 26;27(17):5479.PMID:36080248DOI:10.3390/molecules27175479.
Verbenone and carvone are allylic monoterpenoid ketones with many applications in the fine chemicals industry that can be obtained, respectively, from the allylic oxidation of α-pinene and limonene over a silica-supported iron hexadecachlorinated phthalocyanine (FePcCl16-NH2-SiO2) catalyst and with t-butyl hydroperoxide (TBHP) as oxidant. As there are no reported analyses of the environmental impacts associated with catalytic transformation of terpenes into value-added products that include the steps associated with synthesis of the catalyst and several options of raw materials in the process, this contribution reports the evaluation of the environmental impacts in the conceptual process to produce Verbenone and carvone considering two scenarios (SI-raw-oils and SII-purified-oils). The impact categories were evaluated using ReCiPe and IPCC methods implemented in SimaPro 9.3 software. The environmental impacts in the synthesis of the heterogeneous catalyst FePcCl16-NH2-SiO2 showed that the highest burdens in terms of environmental impact come from the use of fossil fuel energy sources and solvents, which primarily affect human health. The most significant environmental impacts associated with carvone and Verbenone production are global warming and fine particulate matter formation, with fewer environmental impacts associated with the process that starts directly from turpentine and orange oils (SI-raw-oils) instead of the previously extracted α-pinene and limonene (SII-purified-oils). As TBHP was identified as a hotspot in the production process of Verbenone and carvone, it is necessary to choose a more environmentally friendly and energy-efficient oxidizing agent for the oxidation of turpentine and orange oils.
CuAPO-5 as a Multiphase Catalyst for Synthesis of Verbenone from α-Pinene
Materials (Basel) 2022 Nov 16;15(22):8097.PMID:36431582DOI:10.3390/ma15228097.
Copper(II)-containing aluminum phosphate material (CuAPO-5) was synthesized hydrothermally and used as a multiphase catalyst for the oxidation of α-pinene to Verbenone. The catalysts were analyzed using X-ray diffraction (XRD), Brunauer-Emmett-Teller (BET) surface area techniques, X-ray photoelectron spectroscopy (XPS), and ammonia temperature programmed reduction (NH3-TPD). Scanning electron microscopy (SEM), X-ray energy spectrometry (EDS), inductively coupled plasma emission spectroscopy (ICP-OES), Fourier infrared spectroscopy (FT-IR), and ultraviolet-visible spectroscopy (UV-vis) were performed to characterize the material. The effects of reaction temperature, reaction time, n(α-pinene)/n(TBHP), and solvent on the catalytic performance of CuAPO-5 were investigated. The results show that all the prepared catalysts have AFI topology and a large specific surface area. Copper is evenly distributed in the skeleton in a bivalent form. The introduction of copper increases the acid content of the catalyst. Under the optimized reaction conditions, 96.8% conversion of α-pinene and 46.4% selectivity to Verbenone were achieved by CuAPO-5(0.06) molecular sieve within a reaction time of 12 h. CuAPO-5(0.06) can be recycled for five cycles without losing the conversion of α-pinene and the selectivity to Verbenone.
Microhydration of Verbenone: how the chain of water molecules adapts its structure to the host molecule
Phys Chem Chem Phys 2020 Mar 11;22(10):5855-5864.PMID:32107510DOI:10.1039/c9cp06678k.
The microsolvation of Verbenone (C10H14O)·(H2O)n (n = 1, 2, 3) was experimentally investigated in a supersonic expansion using a cavity-based Fourier transform microwave spectrometer, in the 2.8-14 GHz frequency range. Thanks to computationally optimized structures at the B3LYP-D3BJ/def2-TZVP and MP2/6-311++G(d,p) levels using the Gaussian 16 software, the spectra of two mono- and two dihydrates, and that of the lowest energy conformer among the four expected trihydrates, could be assigned. A similar study replacing normal water with 18O labeled water allowed the identification of the spectra of all possible isotopomers, leading to the calculation of the substitution coordinates of water oxygen atoms, and of the effective structure of the water molecule arrangements around Verbenone. The computed rotational constants and structural parameters were found to be quite close to the experimental ones both at the DFT and ab initio levels. A comparison between the structures of the hydrates of camphor previously studied by Pérez et al. [J. Phys. Chem. Lett., 2016, 7, 154-160] and of those of Verbenone shows that the chain of water molecules adapt their structure according to the geometry of the host molecule. The general trend is that bond angles in the water chain are much wider in Verbenone than in camphor.