beta-Ionone (BioDeep_00000009223)

 

Secondary id: BioDeep_00000858408, BioDeep_00000861363

human metabolite PANOMIX_OTCML-2023 Endogenous Volatile Flavor Compounds


代谢物信息卡片


(E)-4-(2,6,6-trimethylcyclohexen-1-yl)but-3-en-2-one

化学式: C13H20O (192.151407)
中文名称: beta-紫罗酮, β-紫罗兰酮, β-紫罗酮
谱图信息: 最多检出来源 Viridiplantae(plant) 0.15%

Reviewed

Last reviewed on 2024-11-06.

Cite this Page

beta-Ionone. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/beta-ionone (retrieved 2024-11-21) (BioDeep RN: BioDeep_00000009223). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CC(/C=C/C1=C(C)CCCC1(C)C)=O
InChI: InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h7-8H,5-6,9H2,1-4H3/b8-7+

描述信息

Beta-ionone is a colorless to light yellow liquid with an odor of cedar wood. In very dilute alcoholic solution the odor resembles odor of violets. Used in perfumery.
Beta-ionone is an ionone that is but-3-en-2-one substituted by a 2,6,6-trimethylcyclohex-1-en-1-yl group at position 4. It has a role as an antioxidant and a fragrance.
beta-Ionone is a natural product found in Nepeta nepetella, Vitis rotundifolia, and other organisms with data available.
beta-Ionone is a metabolite found in or produced by Saccharomyces cerevisiae.
beta-Ionone, also known as (e)-b-ionone or trans-beta-ionone, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
Found in many essential oils including oil of Boronia megastigma (brown boronia) and coml. ionone. Flavouring agent
An ionone that is but-3-en-2-one substituted by a 2,6,6-trimethylcyclohex-1-en-1-yl group at position 4.
D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

β-Ionone is effective in the induction of apoptosis in gastric adenocarcinoma SGC7901 cells. Anti-cancer activity[1].

β-Ionone. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=79-77-6 (retrieved 2024-11-06) (CAS RN: 79-77-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

同义名列表

90 个代谢物同义名

InChI=1/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h7-8H,5-6,9H2,1-4H3/b8-7; 3-Buten-2-one, 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (3E)-; 3-Buten-2-one, 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (E)-; 3-Buten-2-one, 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (E); (3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl) but-3-en-2-one; trans-4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-3-buten-2-one; 4-(2,6,6-Trimethyl-1(or 2)-cyclohexen-1-yl)-3-buten-2-one; (3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one; (3E)-4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-3-buten-2-one; [E]-4-[2,6,6-trimethyl-1-cyclohexen-1-yl]-3-buten-2-one; (E)-4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-3-buten-2-one; 4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-(E)-3-Buten-2-one; (E)-4-(2,6,6-Trimethylcyclohex-1-en-1-yl)but-3-en-2-one; 4-(2,6,6-Trimethylcyclohex-1-ene-1-yl)-but-3-ene-2-one; 3-Buten-2-one, 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-; (E)-4-(2,6,6-trimethyl-1-cyclohexenyl)-but-3-en-2-one; (E)-4-(2,6,6-trimethylcyclohex-1-enyl)but-3-en-2-one; (E)-4-(2,6,6-trimethylcyclohexen-1-yl)but-3-en-2-one; 4-(2,6,6-trimethyl-1-cyclohexene-1-yl)-3-buten-2-one; 4-(2,6,6-Trimethyl-1-cyclohexen-l-yl)-3-buten-2-one; 4-(2,6,6-Trimethylcyclohex-1-en-1-yl)but-3-en-2-one; 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one; 4-(2,6-Trimethyl-1-cyclohexen-1-yl)-3-buten-2-one; beta-Ionone, predominantly trans, >=97\\%, FCC, FG; 4-(2,6-Trimethyl-1-cyclohexen-l-yl)-3-buten-2-one; 4-(2,6,6-Trimethyl-1-cyclohexenyl)-3-buten-2-one; 3-Buten-2-one,6,6-trimethyl-1-cyclohexen-1-yl)-; 4-(2,6-Trimethyl-1-cyclohexenyl)-3-buten-2-one; 2-07-00-00140 (Beilstein Handbook Reference); beta-Ionone, natural (US), >=85\\%, FG; beta-Ionone, purum, >=95.0\\% (GC); beta-Ionone, analytical standard; beta-Ionone, natural, >=85\\%, FG; .beta.-Cyclocitrylideneacetone; beta-Cyclocitrylideneacetone; 3-BENZYLAMINO-PROPIONICACID; BETA-CYCLOCITRYLIDENACETONE; beta-ionone, (trans)-isomer; WLN: L6UTJ A1U1V1 B1 F1 F1; 9-apo-beta-caroten-9-one; .beta.-Ionone isomer # 2; .beta.-Ionone isomer # 1; beta-Ionone, synthetic; .BETA.-IONONE [FHFI]; beta-Ionone (trans); trans-.beta.-Ionone; .BETA.-IONONE [MI]; Trans-beta -ionone; (E)-.beta.-Ionone; beta-Ionone, 96\\%; trans-beta-Ionone; BETA-IONONE [FCC]; (3E)-BETA-IONONE; (E)-beta -ionone; UNII-A7NRR1HLH6; (E)-beta-Ionone; Ionone, .beta.-; beta -E-ionone; trans-b-Ionone; trans-Β-ionone; .beta.-Ionone; .beta.-Ionene; Ionone, beta-; beta-E-Ionone; Tox21_300709; Tox21_302862; (e)-b-Ionone; Tox21_201454; (e)-Β-ionone; IONONE, BETA; beta -ionone; CAS-79-77-6; beta-Ionone; beta-Jonone; beta ionone; A7NRR1HLH6; b-e-Ionone; beta-Ionon; Β-e-ionone; AI3-25073; ss-Ionone; FEMA 2595; ?-IONONE; b-ionone; β-Ionone; Β-ionon; b-Ionon; 4-(2,6,6-Trimethyl-cyclohex-1-enyl)-but-3-en-2-one; beta-Ionone; beta-Ionone



数据库引用编号

23 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(6)

BioCyc(2)

PlantCyc(2)

代谢反应

425 个相关的代谢反应过程信息。

Reactome(93)

BioCyc(4)

WikiPathways(0)

Plant Reactome(195)

INOH(0)

PlantCyc(132)

COVID-19 Disease Map(0)

PathBank(1)

PharmGKB(0)

95 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Cristina Votta, Jian You Wang, Nicola Cavallini, Francesco Savorani, Arianna Capparotto, Kit Xi Liew, Marco Giovannetti, Luisa Lanfranco, Salim Al-Babili, Valentina Fiorilli. Integration of rice apocarotenoid profile and expression pattern of Carotenoid Cleavage Dioxygenases reveals a positive effect of β-ionone on mycorrhization. Plant physiology and biochemistry : PPB. 2024 Feb; 207(?):108366. doi: 10.1016/j.plaphy.2024.108366. [PMID: 38244387]
  • Maria Sol Balbuena, Stephen L Buchmann, Daniel R Papaj, Robert A Raguso. Organ-specific volatiles from Sonoran desert Krameria flowers as potential signals for oil-collecting bees. Phytochemistry. 2024 Feb; 218(?):113937. doi: 10.1016/j.phytochem.2023.113937. [PMID: 38035972]
  • Tingting Shi, Man Shi, Yunfang Ye, Yuanzheng Yue, Lianggui Wang, Xiulian Yang. Floral Volatile Organic Compounds Change the Composition and Function of the Endophytic Fungal Community in the Flowers of Osmanthus fragrans. International journal of molecular sciences. 2024 Jan; 25(2):. doi: 10.3390/ijms25020857. [PMID: 38255929]
  • Abrar Felemban, Juan C Moreno, Jianing Mi, Shawkat Ali, Arjun Sham, Synan F AbuQamar, Salim Al-Babili. The apocarotenoid β-ionone regulates the transcriptome of Arabidopsis thaliana and increases its resistance against Botrytis cinerea. The Plant journal : for cell and molecular biology. 2023 Nov; ?(?):. doi: 10.1111/tpj.16510. [PMID: 37932864]
  • Jixin Zhang, Dongzhou Xia, Tiehan Li, Yuming Wei, Wanzhen Feng, Zhichao Xiong, Junlan Huang, Wei-Wei Deng, Jingming Ning. Effects of different over-fired drying methods on the aroma of Lu'an Guapian tea. Food research international (Ottawa, Ont.). 2023 Nov; 173(Pt 1):113224. doi: 10.1016/j.foodres.2023.113224. [PMID: 37803542]
  • Yuming Wei, Jixin Zhang, Tiehan Li, Mengjie Zhao, Zhenshuo Song, Yujie Wang, Jingming Ning. GC-MS, GC-O, and sensomics analysis reveals the key odorants underlying the improvement of yellow tea aroma after optimized yellowing. Food chemistry. 2023 Aug; 431(?):137139. doi: 10.1016/j.foodchem.2023.137139. [PMID: 37604002]
  • Hiroshi Magome, Masao Arai, Kiyoshi Oyama, Ryo Nishiguchi, Yoshimitsu Takakura. Multiple loss-of-function mutations of carotenoid cleavage dioxygenase 4 reveal its major role in both carotenoid level and apocarotenoid composition in flue-cured mature tobacco leaves. Scientific reports. 2023 08; 13(1):12992. doi: 10.1038/s41598-023-39692-4. [PMID: 37563246]
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  • Hee Ju Yoo, Mi-Young Chung, Hyun-Ah Lee, Soo-Bin Lee, Silvana Grandillo, James J Giovannoni, Je Min Lee. Natural overexpression of CAROTENOID CLEAVAGE DIOXYGENASE 4 in tomato alters carotenoid flux. Plant physiology. 2023 Jan; ?(?):. doi: 10.1093/plphys/kiad049. [PMID: 36715630]
  • Ruijun Li, Shuang Shan, Xuan Song, Adel Khashaveh, Shanning Wang, Zixuan Yin, Ziyun Lu, Khalid Hussain Dhiloo, Yongjun Zhang. Plant volatile ligands for male-biased MmedOBP14 stimulate orientation behavior of the parasitoid wasp Microplitis mediator. International journal of biological macromolecules. 2022 Dec; 223(Pt A):1521-1529. doi: 10.1016/j.ijbiomac.2022.11.149. [PMID: 36400212]
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  • Siyi Du, Haozhe Xu, Mengdan Yang, Ning Pan, Tiefeng Zheng, Chenyi Xu, Yan Li, Zhaojiang Zuo. Toxic mechanism of two cyanobacterial volatiles β-cyclocitral and β-ionone on the photosynthesis in duckweed by altering gene expression. Environmental pollution (Barking, Essex : 1987). 2022 Sep; 308(?):119711. doi: 10.1016/j.envpol.2022.119711. [PMID: 35809713]
  • Weicheng Zhou, Yuming Wang, Jinglong Wang, Chengrong Peng, Zhicong Wang, Hongjie Qin, Genbao Li, Dunhai Li. β-Ionone causes endocrine disruption, hyperpigmentation and hypoactivity in zebrafish early life stages. The Science of the total environment. 2022 Aug; 834(?):155433. doi: 10.1016/j.scitotenv.2022.155433. [PMID: 35461947]
  • Suleiman Aminu, Mohammed Auwal Ibrahim, Gloria Dada Chechet, Elewechi Onyike. Chemotherapeutic potentials of β-ionone against Trypanosoma congolense infection: Inhibition of parasite proliferation, anemia development, trans-sialidase (TconTS3 and TconTS4) gene expressions, and phospholipase A2. Chemical biology & drug design. 2022 06; 99(6):908-922. doi: 10.1111/cbdd.14048. [PMID: 35353953]
  • Alessandro Brambilla, Anna Sommer, Andrea Ghirardo, Marion Wenig, Claudia Knappe, Baris Weber, Melissa Amesmaier, Miriam Lenk, Jörg-Peter Schnitzler, A Corina Vlot. Immunity-associated volatile emissions of β-ionone and nonanal propagate defence responses in neighbouring barley plants. Journal of experimental botany. 2022 01; 73(2):615-630. doi: 10.1093/jxb/erab520. [PMID: 34849759]
  • Lujain Aloum, Mohammad H Semreen, Taleb H Al-Tel, Hamza Al-Hroub, Muath Mousa, Richard L Jayaraj, Eman Alefishat, Abdu Adem, Georg A Petroianu. Metabolic conversion of β-pinene to β-ionone in rats. Xenobiotica; the fate of foreign compounds in biological systems. 2021 Dec; 51(12):1427-1435. doi: 10.1080/00498254.2021.2020376. [PMID: 34931580]
  • Ping Yang, Huanlu Song, Yanping Lin, Tianyang Guo, Lijin Wang, Michael Granvogl, Yongquan Xu. Differences of characteristic aroma compounds in Rougui tea leaves with different roasting temperatures analyzed by switchable GC-O-MS and GC × GC-O-MS and sensory evaluation. Food & function. 2021 Jun; 12(11):4797-4807. doi: 10.1039/d1fo00165e. [PMID: 33861271]
  • Deepa Agarwal, Lim Mui, Emma Aldridge, James McKinney, Louise Hewson, Ian Denis Fisk. The progression of lipid oxidation, β-carotenes degradation and sensory perception of batch-fried sliced sweet potato crisps during storage. Food & function. 2021 May; 12(10):4535-4543. doi: 10.1039/d0fo03100c. [PMID: 33903860]
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  • Jingming Wang, Bin Wu, Na Zhang, Mingyue Zhao, Tingting Jing, Yi Wu, YunQing Hu, Feng Yu, Xiaochun Wan, Wilfried Schwab, Chuankui Song. Dehydration-Induced Carotenoid Cleavage Dioxygenase 1 Reveals a Novel Route for β-Ionone Formation during Tea (Camellia sinensis) Withering. Journal of agricultural and food chemistry. 2020 Sep; 68(39):10815-10821. doi: 10.1021/acs.jafc.0c04208. [PMID: 32840106]
  • Yanting Zhong, Xiaoying Pan, Ruifeng Wang, Jiuliang Xu, Jingyu Guo, Tingxue Yang, Jianyu Zhao, Faisal Nadeem, Xiaoting Liu, Hongyan Shan, Yanjun Xu, Xuexian Li. ZmCCD10a Encodes a Distinct Type of Carotenoid Cleavage Dioxygenase and Enhances Plant Tolerance to Low Phosphate. Plant physiology. 2020 09; 184(1):374-392. doi: 10.1104/pp.20.00378. [PMID: 32586893]
  • Jingming Wang, Na Zhang, Minyue Zhao, Tingting Jing, Jieyang Jin, Bin Wu, Xiaochun Wan, Wilfried Schwab, Chuankui Song. Carotenoid Cleavage Dioxygenase 4 Catalyzes the Formation of Carotenoid-Derived Volatile β-Ionone during Tea (Camellia sinensis) Withering. Journal of agricultural and food chemistry. 2020 Feb; 68(6):1684-1690. doi: 10.1021/acs.jafc.9b07578. [PMID: 31957431]
  • Nicole Werner, César A Ramirez-Sarmiento, Eduardo Agosin. Protein engineering of carotenoid cleavage dioxygenases to optimize β-ionone biosynthesis in yeast cell factories. Food chemistry. 2019 Nov; 299(?):125089. doi: 10.1016/j.foodchem.2019.125089. [PMID: 31319343]
  • Cencen Yu, Chenfei Shi, Jing Tang, Qiuyi Ji, Xuan Wang, Xiaoguang Xu, Guoxiang Wang. Release of taste and odour compounds during Zizania latifolia decay: A microcosm system study. Environmental pollution (Barking, Essex : 1987). 2019 Nov; 254(Pt A):112954. doi: 10.1016/j.envpol.2019.07.122. [PMID: 31398637]
  • Cencen Yu, Chenfei Shi, Ming Ji, Xiaoguang Xu, Zhongqian Zhang, Jie Ma, Guoxiang Wang. Taste and odor compounds associated with aquatic plants in Taihu Lake: distribution and producing potential. Environmental science and pollution research international. 2019 Nov; 26(33):34510-34520. doi: 10.1007/s11356-019-06188-6. [PMID: 31643015]
  • Fengqi Li, Du Li, Youssef Dewer, Cheng Qu, Zhen Yang, Jiahui Tian, Chen Luo. Discrimination of Oviposition Deterrent Volatile β-Ionone by Odorant-Binding Proteins 1 and 4 in the Whitefly Bemisia tabaci. Biomolecules. 2019 10; 9(10):. doi: 10.3390/biom9100563. [PMID: 31623354]
  • Shuang-Feng Sun, Fang-Fang Zeng, Shan-Cheng Yi, Man-Qun Wang. Molecular Screening of Behaviorally Active Compounds with CmedOBP14 from the Rice Leaf Folder Cnaphalocrocis medinalis. Journal of chemical ecology. 2019 Oct; 45(10):849-857. doi: 10.1007/s10886-019-01106-z. [PMID: 31512099]
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