Ocimene
(Synonyms: 罗勒烯) 目录号 : GC41497
A monoterpene
Cas No.:13877-91-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >90.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Ocimene is a monoterpene found in a variety of plants, including Cannabis, and is a volatile compound involved in plant-plant signaling and plant defense against pests. Emission of ocimene from tea (C. sinensis) and L. japonicus plants is induced in response to a jasmonic acid combined with mechanical damage (JAMD) model of herbivore attack and within 24 hours of spider mite (T. urticae) infestation, respectively. Ocimene reduces the number of winged aphids (M. persicae) that settle on Chinese cabbage and the feeding time and number of nymphs produced by aphids on leaves. The aphid endoparasitoid A. gifuensis demonstrates a preference for ocimene-treated Chinese cabbage over control plants in a wind tube two-choice test. Conditioning of tomato plants using volatile organic compounds (VOCs) from transgenic tobacco plants overexpressing β-ocimene synthase increases production of VOCs and reduces the number of aphids (M. euphorbiae) that settle on the plant and the number of nymphs produced by the aphids that settle, as well as increases the number of landings of the aphid parasitoid A. ervi compared with conditioning using wild-type tobacco VOCs. Formulations containing ocimene have been used as fragrance ingredients.
| Cas No. | 13877-91-3 | SDF | |
| 别名 | 罗勒烯 | ||
| Canonical SMILES | C/C(C)=C/C/C=C(C)/C=C | ||
| 分子式 | C10H16 | 分子量 | 136.2 |
| 溶解度 | DMSO : 100 mg/mL (734.05 mM; Need ultrasonic) | 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 | 7.3421 mL | 36.7107 mL | 73.4214 mL |
| 5 mM | 1.4684 mL | 7.3421 mL | 14.6843 mL |
| 10 mM | 0.7342 mL | 3.6711 mL | 7.3421 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。
Shoot Characterization of Isoprene and Ocimene-Emitting Transgenic Arabidopsis Plants under Contrasting Environmental Conditions
Plants (Basel) 2020 Apr 9;9(4):477.PMID:32283654DOI:10.3390/plants9040477.
Isoprenoids are among the most abundant biogenic volatile compounds (VOCs) emitted by plants, and mediate both biotic and abiotic stress responses. Here, we provide for the first time a comparative analysis of transgenic Arabidopsis lines constitutively emitting isoprene and Ocimene. Transgenic lines and Columbia-0 (Col-0) Arabidopsis were characterized under optimal, water stress, and heat stress conditions. Under optimal conditions, the projected leaf area (PLA), relative growth rate, and final dry weight were generally higher in transgenics than Col-0. These traits were associated to a larger photosynthetic capacity and CO2 assimilation rate at saturating light. Isoprene and Ocimene emitters displayed a moderately higher stress tolerance than Col-0, showing higher PLA and gas-exchange traits throughout the experiments. Contrasting behaviors were recorded for the two overexpressors under water stress, with isoprene emitters showing earlier stomatal closure (conservative behavior) than Ocimene emitters (non-conservative behavior), which might suggest different induced strategies for water conservation and stress adaptation. Our work indicates that (i) isoprene and Ocimene emitters resulted in enhanced PLA and biomass under optimal and control conditions and that (ii) a moderate stress tolerance is induced when isoprene and Ocimene are constitutively emitted in Arabidopsis, thus providing evidence of their role as a potential preferable trait for crop improvement.
New Insights into Stress-Induced β-Ocimene Biosynthesis in Tea ( Camellia sinensis) Leaves during Oolong Tea Processing
J Agric Food Chem 2021 Oct 6;69(39):11656-11664.PMID:34554738DOI:10.1021/acs.jafc.1c04378.
As the major contributors to the floral odors of tea products, terpenoid volatiles play critical roles in the defense response of plants to multiple stresses. Until now, only a few TPS genes in tea plants (Camellia sinensis) have been functionally validated. In this study, by comparative studies conducted at gene, protein, and metabolite levels during oolong tea processing, we isolated an Ocimene synthase gene, CsOCS, which displays a low similarity to previously characterized tea Ocimene synthases. Further prokaryotic expression and subcellular localization analysis showed that it is plastid-located and could produce (E)-β-ocimene and (Z)-β-ocimene using GPP as the substrate. The optimum temperature and pH of the enzyme were 30 °C and 7.5, respectively. Treatment with exogenous methyl jasmonate elevated the transcript level of CsOCS and enhanced the emission of Ocimene from tea leaves. Collectively, CsOCS is implicated as a key enzyme for β-ocimene synthesis during oolong tea processing.
Absolute configuration of the Ocimene monoterpenoids from Artemisia absinthium
Chirality 2017 Nov;29(11):716-725.PMID:28840973DOI:10.1002/chir.22741.
The absolute configuration (AC) of the naturally occurring ocimenes (-)-(3S,5Z)-2,6-dimethyl-2,3-epoxyocta-5,7-diene (1) and (-)-(3S,5Z)-2,6-dimethylocta-5,7-dien-2,3-diol (2), isolated from the essential oils of domesticated specimens of Artemisia absinthium, followed by vibrational circular dichroism (VCD) studies of 1, as well as from the acetonide 3 and the monoacetate 4, both derived from 2, since secondary alcohols are not the best functional groups to be present during VCD studies in solution due to intermolecular associations. The AC follows from comparison of experimental and calculated VCD spectra that were obtained by Density Functional Theory computation at the B3LYP/DGDZVP level of theory. Careful nuclear magnetic resonance (NMR) measurements were compared with literature values, providing for the first time systematic 1 H and 13 C chemical shift data. Regarding homonuclear 1 H coupling constants, after performing a few irradiation experiments that showed the presence of several small long-range interactions, the complete set of coupling constants for 3, which is representative of the four studied molecules, was determined by iterations using the PERCH software. This procedure even allowed assigning the pro-R and pro-S methyl group signals of the two gem-dimethyl groups present in 3.
Less is more: Independent loss-of-function Ocimene SYNTHASE alleles parallel pollination syndrome diversification in monkeyflowers (Mimulus)
Am J Bot 2017 Jul;104(7):1055-1059.PMID:28724593DOI:10.3732/ajb.1700104.
Premise of the study: Pollinator-mediated selection on flower phenotypes (e.g., shape, color, scent) is key to understanding the adaptive radiation of angiosperms, many of which have evolved specialized relationships with a particular guild of animal pollinators (e.g., birds, bats, moths, bees). E-β-Ocimene, a monoterpene produced by Ocimene SYNTHASE (OS) in Mimulus lewisii, is a floral scent important in attracting the species' bumblebee pollinators. The taxa closely related to M. lewisii have evolved several different pollination syndromes, including hummingbird pollination and self pollination (autogamy). We are interested in how floral scent variation contributed to species diversification in this clade. Methods: We analyzed variation in E-β-ocimene emission within this Mimulus clade and explored its molecular basis through a combination of DNA sequencing, reverse transcriptase PCR, and enzyme functional analysis in vitro. Key results: We found that none of the taxa, other than M. lewisii, emitted E-β-ocimene from flowers. But the molecular basis underlying loss of E-β-ocimene emission is unique in each taxon, including deletion, missense, or frameshift mutations in the OS gene, and potential posttranscriptional downregulation. Conclusions: The molecular evidence suggests that parallel loss-of-function in OS is the best explanation for the observed pattern of E-β-ocimene emission, likely as the result of natural selection.
In Planta Recapitulation of Isoprene Synthase Evolution from Ocimene Synthases
Mol Biol Evol 2017 Oct 1;34(10):2583-2599.PMID:28637270DOI:10.1093/molbev/msx178.
Isoprene is the most abundant biogenic volatile hydrocarbon compound naturally emitted by plants and plays a major role in atmospheric chemistry. It has been proposed that isoprene synthases (IspS) may readily evolve from other terpene synthases, but this hypothesis has not been experimentally investigated. We isolated and functionally validated in Arabidopsis the first isoprene synthase gene, AdoIspS, from a monocotyledonous species (Arundo donax L., Poaceae). Phylogenetic reconstruction indicates that AdoIspS and dicots isoprene synthases most likely originated by parallel evolution from TPS-b monoterpene synthases. Site-directed mutagenesis demonstrated invivo the functional and evolutionary relevance of the residues considered diagnostic for IspS function. One of these positions was identified by saturating mutagenesis as a major determinant of substrate specificity in AdoIspS able to cause invivo a dramatic change in total volatile emission from hemi- to monoterpenes and supporting evolution of isoprene synthases from Ocimene synthases. The mechanism responsible for IspS neofunctionalization by active site size modulation by a single amino acid mutation demonstrated in this study might be general, as the very same amino acidic position is implicated in the parallel evolution of different short-chain terpene synthases from both angiosperms and gymnosperms. Based on these results, we present a model reconciling in a unified conceptual framework the apparently contrasting patterns previously observed for isoprene synthase evolution in plants. These results indicate that parallel evolution may be driven by relatively simple biophysical constraints, and illustrate the intimate molecular evolutionary links between the structural and functional bases of traits with global relevance.