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cis-3-Hexenyl hexanoate

(Synonyms: (Z)-3-hexenyl hexanoate) 目录号 : GC25258

Cis-3-Hexenyl hexanoate ((Z)-3-hexenyl hexanoate) is a kind of plant volatile that brings tropical and pulpy profile with citrus and green nuances to all kinds of fruit flavors

cis-3-Hexenyl hexanoate Chemical Structure

Cas No.:31501-11-8

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100mg
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产品描述

Cis-3-Hexenyl hexanoate ((Z)-3-hexenyl hexanoate) is a kind of plant volatile that brings tropical and pulpy profile with citrus and green nuances to all kinds of fruit flavors.

[1] Zhao-Qun Li, et al. J Insect Physiol. Nov-Dec 2018;111:25-31.

Chemical Properties

Cas No. 31501-11-8 SDF Download SDF
别名 (Z)-3-hexenyl hexanoate
分子式 C12H22O2 分子量 198.3
溶解度 DMSO : 100 mg/mL (504.29 mM; Need ultrasonic) 储存条件 Store at -20°C
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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。
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溶解性数据

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1 mg 5 mg 10 mg
1 mM 5.0429 mL 25.2143 mL 50.4286 mL
5 mM 1.0086 mL 5.0429 mL 10.0857 mL
10 mM 0.5043 mL 2.5214 mL 5.0429 mL
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Research Update

Characterization of Key Odorants in Xinyang Maojian Green Tea and Their Changes During the Manufacturing Process

J Agric Food Chem 2022 Jan 12;70(1):279-288.PMID:34932338DOI:10.1021/acs.jafc.1c06473.

Xinyang Maojian (XYMJ) green tea is a famous high-grade Chinese green tea, but the key odorants contributing to its aroma have been poorly understood. In this study, solid-phase microextraction and solvent-assisted flavor evaporation were used for sample preparation, and gas chromatography-mass spectrometry (GC-MS) and gas chromatography-olfactometry (GC-O) were used for both qualitative and quantitative analysis. A total of 50 volatile compounds of five chemical classes were identified in XYMJ tea infusion. Among them, nine odorants including nonanal, β-ionone, octanal, E-nerolidol, linalool, cis-3-Hexenyl hexanoate, geraniol, decanal, and β-cyclocitral were identified as key odorants of XYMJ based on GC-O, odor activity values, and aroma combination experiments. Changes in the content of these aroma-active compounds during the manufacturing process of XYMJ (fresh leaves, fixing, rolling, shaping, and drying) were also determined. Most aroma-active compounds decreased after the fixation process, with the exception of cis-3-Hexenyl hexanoate. This is the first study to investigate the key odorants in XYMJ using the sensomics approach. The findings of this study provide novel information on the aroma quality of XYMJ.

Evaluation of the Volatile Composition and Sensory Behavior of Habanero Pepper during Lactic Acid Fermentation by L. plantarum

Foods 2022 Nov 12;11(22):3618.PMID:36429209DOI:10.3390/foods11223618.

Habanero pepper is recognized for its appealing aroma and flavor. Lactic acid fermentation can improve these sensory properties, especially aroma, by the synthesis of volatile compounds, which might also increase the consumer preference. Thus, the aim of this research was to compare the volatile composition as well as different sensory parameters such as preference and emotions related to the lactic acid fermentation of Habanero pepper by two strains (wild and commercial) of Lactiplantibacillus plantarum. A multiple factor ANOVA was used to compare the volatile composition with different fermentation times and strains. The results demonstrated that the interaction between the strain and fermentation time had significant effects on the volatile compound production that includes 1-hexanol, cis-3-Hexenyl hexanoate, linalool, and 3,3 dimethyl-1-hexanol while only time influenced the production of trans-2-hexen-1-al. The wild strain (WIL) at 48 h of fermentation produced the highest concentration of 3,3 dimethyl-1-hexanol and trans-2-hexen-1-al. On the other hand, the commercial strain (COM) presented the highest concentration of 1-hexanol and cis-3-Hexenyl hexanoate with a 72 h fermentation. The most preferred sample was that fermented by WIL for 48 h for the attribute of odor, while for taste, the most preferred sample was that fermented for 72 h with COM.

Dynamic Changes of Volatile Compounds during the Xinyang Maojian Green Tea Manufacturing at an Industrial Scale

Foods 2022 Sep 2;11(17):2682.PMID:36076866DOI:10.3390/foods11172682.

Xinyang Maojian (XYMJ) is one of the premium green teas and originates from Xinyang, which is the northernmost green tea production area in China. The special geographic location, environmental conditions, and manufacturing process contribute to the unique flavor and rich nutrition of XYMJ green tea. Aroma is an important quality indicator in XYMJ green tea. In order to illustrate the aroma of XYMJ green tea, the key odorants in XYMJ green tea and their dynamic changes during the manufacturing processes were analyzed by headspace solid-phase microextraction (HS-SPME) combined with gas chromatography-mass spectrometry (GC-MS). A total of 73 volatile compounds of six different chemical classes were identified in the processed XYMJ green tea samples, and the manufacturing processes resulted in the losses of total volatile compounds. Among the identified volatile compounds, twenty-four aroma-active compounds, such as trans-nerolidol, geranylacetone, nonanal, (+)-δ-cadinene, linalool, (Z)-jasmone, cis-3-hexenyl butyrate, cis-3-Hexenyl hexanoate, methyl jasmonate, and β-ocimene, were identified as the key odorants of XYMJ green tea based on odor activity value (OAV). The key odorants are mainly volatile terpenes (VTs) and fatty acid-derived volatiles (FADVs). Except for (+)-δ-cadinene, copaene, cis-β-farnesene, (Z,E)-α-farnesene and phytol acetate, the key odorants significantly decreased after fixing. The principal coordinate analysis (PCoA) and the hierarchical cluster analysis (HCA) analyses suggested that fixing was the most important manufacturing process for the aroma formation of XYMJ green tea. These findings of this study provide meaningful information for the manufacturing and quality control of XYMJ green tea.

Crystal structure and ligand identification of odorant binding protein 4 in the natural predator Chrysopa pallens

Int J Biol Macromol 2019 Dec 1;141:1004-1012.PMID:31525411DOI:10.1016/j.ijbiomac.2019.09.043.

Green lacewing Chrysopa pallens (Rambur) is a general predator of many agricultural pests and plays a pivotal role in reducing crop damage by managing insect pest populations. Odorant binding proteins (OBPs) in insects can sense the semiochemicals in the environment and initiate the delivery of signals to their receptors. However, no Chrysopa pallens OBP (CpalOBP) structure has been reported yet, and their corresponding candidate semiochemicals are still largely unknown. Here, we reported the structure of CpalOBP4 solved with X-ray diffraction and showed its potential ligands. Our results showed that CpalOBP4 has a classical OBP structure with six α-helices and three disulfide bridges, and it can bind with farnesene, 2-tridecanone, cis-3-Hexenyl hexanoate, nerolidol and farnesol through a central hydrophobic cavity. Our molecular docking results showed that Met31, Met78, Leu98, Phe141, Leu142 and Pro143 in the hydrophobic cavity were the key residues mediating the interaction of CpalOBP4 with farnesene, 2-tridecanone and cis-3-Hexenyl hexanoate, which was further proven by the results that mutations of these residues led to significantly reduced binding affinities of CpalOBP4 for these ligands. Our study provides useful information for the further investigation of the biological function of CpalOBP4 as well as important cues for improving biological control in agriculture.

Odorant-binding proteins display high affinities for behavioral attractants and repellents in the natural predator Chrysopa pallens

Comp Biochem Physiol A Mol Integr Physiol 2015 Jul;185:51-7.PMID:25810363DOI:10.1016/j.cbpa.2015.03.011.

Chrysopa pallens is an important natural predator of various pests in many different cropping systems. Understanding the sophisticated olfactory system of insect antennae is crucial for studying the physiological bases of olfaction and could also help enhance the effectiveness of C. pallens in biological control. However, functional studies of the olfactory genes in C. pallens are still lacking. In this study, we cloned five odorant-binding protein (OBP) genes from C. pallens (CpalOBPs). Quantitative RT-PCR results indicated that the five CpalOBPs had different tissue expression profiles. Ligand-binding assays showed that farnesol, farnesene, cis-3-Hexenyl hexanoate, geranylacetone, beta-ionone, octyl aldehyde, decanal, nerolidol (Ki<20 μM), and especially 2-pentadecanone (Ki=1.19 μM) and 2-hexyl-1-decanol (Ki=0.37 μM) strongly bound to CpalOBP2. CpalOBP15 exhibited high binding affinities for beta-ionone, 2-tridecanone, trans-nerolidol, and dodecyl aldehyde. Behavioral trials using the 14 compounds exhibiting high binding affinities for the CpalOBPs revealed that nine were able to elicit significant behavioral responses from C. pallens. Among them, farnesene and its corresponding alcohol, farnesol, elicited remarkable repellent behavioral responses from C. pallens. Our study provides several compounds that could be selected to develop slow-release agents that attract/repel C. pallens and to improve the search for strategies to eliminate insect pests.