cis-Jasmone
(Synonyms: 顺式茉莉酮) 目录号 : GC35699
Cis-Jasmone 是一种植物来源的天然产物。Cis-Jasmone 由许多花组成型释放，有时通过叶子作为传粉者的引诱剂或作为昆虫花食草动物宿主定位的化学提示。Cis-Jasmone 处理作物不仅可以诱导对食草动物的直接防御，还可以通过释放吸收天敌的挥发性有机化合物来诱导间接防御。
Cas No.:488-10-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Cis-Jasmone is a plant-derived natural product. Cis-Jasmone is constitutively released by many flowers and sometimes by leaves as an attractant for pollinators or as a chemical cue for host location by insect flower herbivores. Cis-Jasmone treatment of crop plants not only induces direct defense against herbivores, but also induces indirect defense by releasing VOCs that attract natural enemies[1].
[1]. Sobhy IS, et al. cis-Jasmone Elicits Aphid-Induced Stress Signalling in Potatoes. J Chem Ecol. 2017 Jan;43(1):39-52.
| Cas No. | 488-10-8 | SDF | |
| 别名 | 顺式茉莉酮 | ||
| Canonical SMILES | O=C1C(C/C=C/CC)=C(C)CC1 | ||
| 分子式 | C11H16O | 分子量 | 164.24 |
| 溶解度 | Soluble in DMSO | 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 | 6.0887 mL | 30.4433 mL | 60.8865 mL |
| 5 mM | 1.2177 mL | 6.0887 mL | 12.1773 mL |
| 10 mM | 0.6089 mL | 3.0443 mL | 6.0887 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。
Fragrance material review on cis-Jasmone
Food Chem Toxicol 2012 Oct;50 Suppl 3:S613-8.PMID:22445665DOI:10.1016/j.fct.2012.03.026.
A toxicologic and dermatologic review of cis-Jasmone when used as a fragrance ingredient is presented. cis-Jasmone is a member of the fragrance structural group ketones cyclopentanones and cyclopentenones. The common characteristic structural element of the group members is a cyclopentanone or cyclopentenone ring with a straight or branched chain alkane or alkene substituent. This review contains a detailed summary of all available toxicology and dermatology papers that are related to this individual fragrance ingredient and is not intended as a stand-alone document. Available data for cis-Jasmone were evaluated then summarized and includes physical properties, acute toxicity, skin irritation, mucous membrane (eye) irritation, skin sensitization, phototoxicity, photoallergy, and genotoxicity data. A safety assessment of the entire ketones cyclopentanones and cyclopentenones will be published simultaneously with this document; please refer to Belsito et al. (2012) for an overall assessment of the safe use of this material and all ketones cyclopentanones and cyclopentenones in fragrances.
cis-Jasmone Elicits Aphid-Induced Stress Signalling in Potatoes
J Chem Ecol 2017 Jan;43(1):39-52.PMID:28130741DOI:10.1007/s10886-016-0805-9.
Elicitation of plant defense signaling that results in altered emission of volatile organic compounds (VOCs) offers opportunities for protecting plants against arthropod pests. In this study, we treated potato, Solanum tuberosum L., with the plant defense elicitor cis-Jasmone (CJ), which induces the emission of defense VOCs and thus affects the behavior of herbivores. Using chemical analysis, electrophysiological and behavioral assays with the potato-feeding aphid Macrosiphum euphorbiae, we showed that CJ treatment substantially increased the emission of defense VOCs from potatoes compared to no treatment. Coupled GC-electroantennogram (GC-EAG) recordings from the antennae of M. euphorbiae showed robust responses to 14 compounds present in induced VOCs, suggesting their behavioral role in potato/aphid interactions. Plants treated with CJ and then challenged with M. euphorbiae were most repellent to alate M. euphorbiae. Principal component analysis (PCA) of VOC collections suggested that (E)-2-hexenal, (E,E)-4,8,12-trimethyl-1,3,7,11-tridecatetraene (TMTT), (E)-β-farnesene, (E)-4,8-dimethyl-1,3,7-nonatriene (DMNT), methyl salicylate (MeSA), CJ, and methyl benzoate (MeBA) were the main VOCs contributing to aphid behavioral responses, and that production of TMTT, (E)-β-farnesene, CJ, and DMNT correlated most strongly with aphid repellency. Our findings confirm that CJ can enhance potato defense against aphids by inducing production of VOCs involved in aphid-induced signalling.
cis-Jasmone induces accumulation of defence compounds in wheat, Triticum aestivum
Phytochemistry 2008 Jan;69(1):9-17.PMID:17681563DOI:10.1016/j.phytochem.2007.06.020.
Liquid phase extraction (LPE) and vapor phase extraction (VPE) methodologies were used to evaluate the impact of the plant activator, cis-Jasmone, on the secondary metabolism of wheat, Triticum aestivum, var. Solstice. LPE allowed the measurement of benzoxazinoids, i.e. 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA), 2-hydroxy-7-methoxy-1,4-benzoxazin-3-one (HMBOA) and 6-methoxy-benzoxazolin-2-one (MBOA), and phenolic acids such as trans-p-coumaric acid, syringic acid, p-hydroxybenzoic acid, vanillic acid and cis- and trans-ferulic acid. Using LPE, a significantly higher level of DIMBOA was found in aerial parts and roots of T. aestivum following treatment with cis-Jasmone, when compared with untreated plants. Similar results were obtained for phenolic acids, such as trans-ferulic acid and vanillic acid in roots. Using VPE, it was possible to measure levels of 2-hydroxy-7-methoxy-(2H)-1,4-benzoxazin-3(4H)-one (HBOA), benzoxazolin-2(3H)-one (BOA), ferulic acid, syringic acid and coumaric acid. The levels of HBOA in aerial parts and roots were significantly greater in cis-Jasmone treated plants compared to untreated plants. cis-Jasmone is known to be a plant activator in terms of production of defence-related volatile semiochemicals that repel aphids and increase the foraging activity of aphid parasitoids. These results show, for the first time, that cis-Jasmone also induces selective production of secondary metabolites that are capable of directly reducing development of pests, diseases and weeds.
Synthetic cis-Jasmone exposure induces wheat and barley volatiles that repel the pest cereal leaf beetle, Oulema melanopus L
J Chem Ecol 2013 May;39(5):620-9.PMID:23588742DOI:10.1007/s10886-013-0281-4.
The plant semiochemical cis-Jasmone primes/induces plant resistance that deters herbivores and attracts natural enemies. We studied the induction of volatile organic compounds (VOCs) in winter wheat and spring barley after exposure of plants to three synthetic cis-Jasmone doses (50 μl of 1, 100, and 1 × 10(4) ng μl(-1)) and durations of exposure (1, 3, and 6 h). Cereal leaf beetle, Oulema melanopus, adult behavioral responses were examined in a Y-tube olfactometer to cis-Jasmone induced plant VOC bouquets and to two synthetic blends of VOCs (3 green leaf volatiles (GLVs); 4 terpenes + indole). In both cereals, eight VOCs [(Z)-3-hexanal, (Z)-3-hexanol, (Z)-3-hexanyl acetate, (Z)-β-ocimene, linalool, β-caryophyllene, (E)-ß-farnesene, and indole] were induced 100- to 1000-fold after cis-Jasmone exposure. The degree of induction in both cereals was usually positively and linearly associated with increasing exposure dose and duration. However, VOC emission rate was only ~2-fold greater from plants exposed to the highest vs. lowest cis-Jasmone exposure doses (1 × 10(4) difference) or durations (6-fold difference). Male and female O. melanopus were deterred by both cereal VOC bouquets after plant exposure to the high cis-Jasmone dose (1 × 10(4) ng μl(-1)), while females were also deterred after plant exposure to the low dose (1 ng μl(-1)) but attracted to unexposed plant VOC bouquets. Both O. melanopus sexes were repelled by terpene/indole and GLV blends at two concentrations (25 ng · min(-1); 125 ng · min(-1)), but attracted to the lowest dose (1 ng · min(-1)) of a GLV blend. It is possible that the biologically relevant low cis-Jasmone dose has ecological activity and potential for inducing field crop VOCs to deter O. melanopus.
cis-Jasmone treatment induces resistance in wheat plants against the grain aphid, Sitobion avenae (Fabricius) (Homoptera: Aphididae)
Pest Manag Sci 2003 Sep;59(9):1031-6.PMID:12974355DOI:10.1002/ps.730.
cis-Jasmone is a plant volatile known to have roles as an insect semiochemical and in inducing plant defence. It was evaluated in laboratory and field trials for control of cereal aphids. In an olfactometer bioassay cis-Jasmone was repellent to alatae of the grain aphid, Sitobion avenae (Fabricius) (Homoptera: Aphididae). Moreover, wheat, Triticum aestivum (L), seedlings sprayed with formulated cis-Jasmone 24 h previously were less susceptible to attack by S. avenae than control plants. In field simulator studies, significantly fewer alate S. avenae settled on cis-jasmone-treated plants over a 24-h period. In addition, the intrinsic rate of population increase, r(m), of S. avenae apterae was reduced on cis-Jasmone treated seedlings. In a series of small-plot experiments conducted over four years, cis-Jasmone applications reduced cereal aphid populations infesting wheat in the field.