gamma-Terpinene (BioDeep_00000001101)

 

Secondary id: BioDeep_00000001100, BioDeep_00000400455, BioDeep_00000859459

natural product human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


1-Isopropyl-4-methyl-1,4-cyclohexadiene, p-Mentha-1,4-diene

化学式: C10H16 (136.1252)
中文名称: GAMMA-萜品烯,松油烯, γ-松油烯, γ-萜品烯
谱图信息: 最多检出来源 Homo sapiens(plant) 15.14%

分子结构信息

SMILES: C1(=CCC(C)=CC1)C(C)C
InChI: InChI=1/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,7-8H,5-6H2,1-3H3

描述信息

Gamma-terpinene is one of three isomeric monoterpenes differing in the positions of their two double bonds (alpha- and beta-terpinene being the others). In gamma-terpinene the double bonds are at the 1- and 4-positions of the p-menthane skeleton. It has a role as an antioxidant, a plant metabolite, a volatile oil component and a human xenobiotic metabolite. It is a monoterpene and a cyclohexadiene.
gamma-Terpinene is a natural product found in Teucrium montanum, Xylopia aromatica, and other organisms with data available.
The terpinenes are three isomeric hydrocarbons that are classified as terpenes. Gamma-terpinene is one these three isomeric hydrocarbons. It is natural and has been isolated from a variety of plant sources (Wikipedia). It is a major component of essential oils made from Citrus Fruits and has strong antioxidant activity. It has a lemon odor and widely used in food, flavours, soaps, cosmetics, pharmaceutical, tabacco, confectionery and perfume industries (http://www.gyanflavoursexport.com).
See also: Lemon oil, cold pressed (part of); Coriander Oil (part of); Mandarin oil (part of).
Gamma-terpinene is one of four isomeric monoterpenes (the other three being alpha terpinene, beta terpinene and delta terpinene). It is a naturally occurring terpinene and has been isolated from a variety of plant sources. It has the highest boiling point of the four known terpinene isomers. It is a major component of essential oils made from citrus fruits and has a strong antioxidant activity. It has a lemon-like or lime-like odor and is widely used in food, flavours, soaps, cosmetics, pharmaceutical, tabacco, confectionery and perfume industries (http://www.gyanflavoursexport.com). The other isomers of gamma-terpinene, such as alpha-terpinene and delta-terpinene, have been isolated from cardamom and marjoram oils while beta terpinene appears to have no natural source.
One of three isomeric monoterpenes differing in the positions of their two double bonds (alpha- and beta-terpinene being the others). In gamma-terpinene the double bonds are at the 1- and 4-positions of the p-menthane skeleton.
Constituent of many essential oils e.g. Citrus, Eucalyptus, Mentha, Pinus subspecies Ajowan seed oil (Carum copticum) is a major source
γ-Terpinene, a monoterpene, is an orally active antioxidant compound which can scavenge radicals directly. γ-Terpinene has potent antinociception activity[1].
γ-Terpinene, a monoterpene, is an orally active antioxidant compound which can scavenge radicals directly. γ-Terpinene has potent antinociception activity[1].

同义名列表

58 个代谢物同义名

InChI=1/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,7-8H,5-6H2,1-3H; gamma-Terpinene, primary pharmaceutical reference standard; 1,4-Cyclohexadiene, 1-methyl-4-(1-methylethyl)-; 1-Methyl-4-(1-methylethyl)-1,4-cyclohexadiene; 1-methyl-4-(propan-2-yl)cyclohexa-1,4-diene; 1-methyl-4-propan-2-ylcyclohexa-1,4-diene; 1-Isopropyl-4-methyl-1,4-cyclohexadiene #; 1,4-Cyclohexadiene, 1-methyl-4-isopropyl-; 1-isopropyl-4-methyl-cyclohexa-1,4-diene; 1-Methyl-4-isopropyl-1,4-cyclohexadiene; 1-Isopropyl-4-methyl-1,4-cyclohexadiene; 1-isopropyl-4-methylcyclohexa-1,4-diene; 4-Isopropyl-1-methyl-1,4-cyclohexadiene; 1-Methyl-4-isopropylcyclohexadiene-1,4; gamma-Terpinene, purum, >=97.0\\% (GC); gamma-Terpinene, analytical standard; gamma-Terpinene, natural, 95\\%, FG; Gamma-terpinene gamma-terpinene; gamma-Terpinene, >=95\\%, FG; gamma-Terpinene (natural); P-MENTHA-1,4-DIENE [FHFI]; 1, 1-methyl-4-isopropyl-; WLN: L6U CUTJ AY1&1 D1; gamma-Terpinene, 97\\%; GAMMA-TERPINENE [FCC]; Terpinene, .gamma.-; p-Mentha-1,4-diene; .gamma.-Terpinene; 1,4-p-menthadiene; .gamma.-Terpinen; gamma -Terpinene; TERPINENE, ALPHA; UNII-4YGF4PQP49; gamma-terpinene; alpha-Terpinene; Gamma terpinene; Alpha terpinene; beta-terpinene; gamma-Terpinen; Tox21_300963; α terpinene; g-Terpinene; γ-Terpinene; CAS-99-85-4; γ-Terpinen; 4YGF4PQP49; -terpinene; AI3-26468; Terpinene; Crithmene; 1ST1650; Moslene; |A-TPN; 9NI; 1-Isopropyl-4-methyl-1,4-cyclohexadiene, p-Mentha-1,4-diene; γ-Terpinene; gamma-Terpinene; gamma-Terpinene



数据库引用编号

30 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

472 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。

亚细胞结构定位 关联基因列表
Cytoplasm 9 ALOX5, ARHGAP45, BCL2, CASP3, CAT, ELANE, HPGDS, PTGS2, TYR
Peripheral membrane protein 4 ACHE, ALOX5, CYP1B1, PTGS2
Endoplasmic reticulum membrane 4 BCL2, CYP1B1, HMGCR, PTGS2
Nucleus 4 ACHE, BCL2, CASP3, PARP1
cytosol 8 ALOX5, ARHGAP45, BCL2, CASP3, CAT, ELANE, HPGDS, PARP1
nuclear body 1 PARP1
phagocytic vesicle 1 ELANE
nucleoplasm 4 ALOX5, CASP3, HPGDS, PARP1
Cell membrane 3 ACHE, TNF, TRPV1
ruffle membrane 1 ARHGAP45
Multi-pass membrane protein 2 HMGCR, TRPV1
Synapse 1 ACHE
cell surface 3 ACHE, ELANE, TNF
glutamatergic synapse 1 CASP3
Golgi apparatus 2 ACHE, ATRN
lysosomal membrane 1 GAA
neuromuscular junction 1 ACHE
neuronal cell body 3 CASP3, TNF, TRPV1
Cytoplasm, cytosol 2 ALOX5, PARP1
Lysosome 2 GAA, TYR
plasma membrane 7 ACHE, ARHGAP45, ATRN, BCHE, GAA, TNF, TRPV1
Membrane 9 ACHE, ARHGAP45, BCL2, CAT, CYP1B1, GAA, HMGCR, PARP1, TRPV1
caveola 1 PTGS2
extracellular exosome 4 ATRN, CAT, ELANE, GAA
Lysosome membrane 1 GAA
endoplasmic reticulum 3 BCL2, HMGCR, PTGS2
extracellular space 8 ACHE, ALOX5, ATRN, BCHE, ELANE, IL10, IL6, TNF
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 3 ACHE, ALOX5, TYR
mitochondrion 4 BCL2, CAT, CYP1B1, PARP1
protein-containing complex 4 BCL2, CAT, PARP1, PTGS2
intracellular membrane-bounded organelle 5 CAT, CYP1B1, GAA, HPGDS, TYR
Microsome membrane 2 CYP1B1, PTGS2
postsynaptic density 1 CASP3
Single-pass type I membrane protein 2 ATRN, TYR
Secreted 5 ACHE, BCHE, GAA, IL10, IL6
extracellular region 10 ACHE, ALOX5, ARHGAP45, BCHE, CAT, ELANE, GAA, IL10, IL6, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
[Isoform 2]: Secreted 1 ATRN
mitochondrial matrix 1 CAT
Extracellular side 1 ACHE
transcription regulator complex 1 PARP1
Nucleus membrane 2 ALOX5, BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 2 ALOX5, BCL2
external side of plasma membrane 2 TNF, TRPV1
nucleolus 1 PARP1
Melanosome membrane 1 TYR
Golgi-associated vesicle 1 TYR
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
postsynaptic membrane 1 TRPV1
Cell projection, ruffle membrane 1 ARHGAP45
Cytoplasm, perinuclear region 1 ALOX5
Membrane raft 1 TNF
pore complex 1 BCL2
focal adhesion 1 CAT
GABA-ergic synapse 1 TRPV1
Peroxisome 1 CAT
basement membrane 1 ACHE
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 2 CAT, HMGCR
collagen-containing extracellular matrix 1 ELANE
secretory granule 1 ELANE
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Postsynaptic cell membrane 1 TRPV1
Cell projection, neuron projection 1 TRPV1
neuron projection 1 PTGS2
chromatin 1 PARP1
phagocytic cup 1 TNF
Chromosome 1 PARP1
Nucleus, nucleolus 1 PARP1
nuclear replication fork 1 PARP1
chromosome, telomeric region 1 PARP1
blood microparticle 1 BCHE
Lipid-anchor, GPI-anchor 1 ACHE
site of double-strand break 1 PARP1
[Isoform 3]: Secreted 1 ATRN
nuclear envelope 2 ALOX5, PARP1
Nucleus envelope 1 ALOX5
tertiary granule membrane 1 GAA
Melanosome 1 TYR
side of membrane 1 ACHE
myelin sheath 1 BCL2
Peroxisome membrane 1 HMGCR
ficolin-1-rich granule lumen 2 ALOX5, CAT
secretory granule lumen 3 ALOX5, ARHGAP45, CAT
endoplasmic reticulum lumen 3 BCHE, IL6, PTGS2
nuclear matrix 1 ALOX5
transcription repressor complex 1 ELANE
specific granule lumen 1 ELANE
azurophil granule membrane 1 GAA
azurophil granule lumen 2 ARHGAP45, ELANE
Nucleus matrix 1 ALOX5
nuclear envelope lumen 2 ALOX5, BCHE
synaptic cleft 1 ACHE
protein-DNA complex 1 PARP1
ficolin-1-rich granule membrane 1 GAA
death-inducing signaling complex 1 CASP3
[Isoform 1]: Cell membrane 1 ATRN
Cytoplasmic vesicle, phagosome 1 ELANE
site of DNA damage 1 PARP1
Cell projection, dendritic spine membrane 1 TRPV1
dendritic spine membrane 1 TRPV1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
interleukin-6 receptor complex 1 IL6
[Poly [ADP-ribose] polymerase 1, processed N-terminus]: Chromosome 1 PARP1
[Poly [ADP-ribose] polymerase 1, processed C-terminus]: Cytoplasm 1 PARP1
Nucleus intermembrane space 1 ALOX5
autolysosome lumen 1 GAA
BAD-BCL-2 complex 1 BCL2
[Isoform H]: Cell membrane 1 ACHE
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Neha Gupta, Soham Bhattacharya, Adrish Dutta, Jan Tauchen, Přemysl Landa, Klára Urbanová, Markéta Houdková, Eloy Fernández-Cusimamani, Olga Leuner. Synthetic polyploidization induces enhanced phytochemical profile and biological activities in Thymus vulgaris L. essential oil. Scientific reports. 2024 03; 14(1):5608. doi: 10.1038/s41598-024-56378-7. [PMID: 38454146]
  • Karolina A Wojtunik-Kulesza, Anna Oniszczuk. Ability of Selected Monoterpenes to Reduce Fe(III) Ions Being Pro-Neurodegenerative Factors: Tests Based on a FRAP Reaction Extended to 48 Hours. International journal of molecular sciences. 2024 Feb; 25(4):. doi: 10.3390/ijms25042191. [PMID: 38396868]
  • Yu-Xiang Weng, Hsiao-Chi Wang, Yung-Lin Chu, Yun-Zhen Wu, Jie-An Liao, Zheng-Yuan Su. Essential oil from Citrus depressa peel exhibits antimicrobial, antioxidant and cancer chemopreventive effects. Journal of the science of food and agriculture. 2024 Jan; ?(?):. doi: 10.1002/jsfa.13280. [PMID: 38252712]
  • Prem Pratap Singh, Atul Kumar Jaiswal, Ritu Singh, Akshay Kumar, Vishal Gupta, Tanya Singh Raghuvanshi, Angad Sharma, Bhanu Prakash. Assessment of Trachyspermum ammi essential oil against Aspergillus flavus, aflatoxin B1 contamination, and post-harvest quality of Sorghum bicolor. Food chemistry. 2024 Jan; 443(?):138502. doi: 10.1016/j.foodchem.2024.138502. [PMID: 38306909]
  • Dalila Touhami, Adedayo O Mofikoya, Robbie D Girling, Ben Langford, Pawel K Misztal, Christian Pfrang. Atmospheric Degradation of Ecologically Important Biogenic Volatiles: Investigating the Ozonolysis of (E)-β-Ocimene, Isomers of α and β-Farnesene, α-Terpinene and 6-Methyl-5-Hepten-2-One, and Their Gas-Phase Products. Journal of chemical ecology. 2024 Jan; ?(?):. doi: 10.1007/s10886-023-01467-6. [PMID: 38195852]
  • Diana Di Liberto, Nicolò Iacuzzi, Giovanni Pratelli, Antonella Porrello, Antonella Maggio, Salvatore La Bella, Anna De Blasio, Antonietta Notaro, Antonella D'Anneo, Sonia Emanuele, Federica Affranchi, Michela Giuliano, Marianna Lauricella, Daniela Carlisi. Cytotoxic Effect Induced by Sicilian Oregano Essential Oil in Human Breast Cancer Cells. Cells. 2023 11; 12(23):. doi: 10.3390/cells12232733. [PMID: 38067161]
  • Hind Zejli, Aziza Fitat, Youssra Lefrioui, Farhan Siddique, Mohammed Bourhia, Fatima Zahra Bousseraf, Ahmad Mohammad Salamatullah, Hiba-Allah Nafidi, Amare Bitew Mekonnen, Abdelkader Gourch, Mustapha Taleb, Abdelfattah Abdellaoui. Phytochemical analysis and biological activities of essential oils extracted from Origanum grossii and Thymus pallidus: in vitro and in silico analysis. Scientific reports. 2023 11; 13(1):20021. doi: 10.1038/s41598-023-47215-4. [PMID: 37973884]
  • Ferhan Balci-Torun, İrem Toprakçı, Nahide Gulşah Deniz, Sinem Ortaboy, Mehmet Torun, Selin Şahin. Development of an optimized method to obtain a limonene-rich concentrate from the discarded lemon peels. Chemistry & biodiversity. 2023 Jul; ?(?):e202300767. doi: 10.1002/cbdv.202300767. [PMID: 37423898]
  • Aimé Vázquez, Nurhayat Tabanca, Paul E Kendra. HPTLC Analysis and Chemical Composition of Selected Melaleuca Essential Oils. Molecules (Basel, Switzerland). 2023 May; 28(9):. doi: 10.3390/molecules28093925. [PMID: 37175338]
  • Meiyu Sun, Ningning Liu, Jiahui Miao, Yanan Zhang, Yuanpeng Hao, Jinzheng Zhang, Hui Li, Hongtong Bai, Lei Shi. Creation of New Oregano Genotypes with Different Terpene Chemotypes via Inter- and Intraspecific Hybridization. International journal of molecular sciences. 2023 Apr; 24(8):. doi: 10.3390/ijms24087320. [PMID: 37108486]
  • Mudasir Hafiz Khan, Niyaz Ahmad Dar, Bashir Ahmad Alie, Sher Ahmad Dar, Ajaz Ahmad Lone, Ghulam Hassan Mir, Uzma Fayaz, Sajad Ali, Anshika Tyagi, Mohamed A El-Sheikh, Saleh Alansi. Unraveling the Variability of Essential Oil Composition in Different Accessions of Bunium persicum Collected from Different Temperate Micro-Climates. Molecules (Basel, Switzerland). 2023 Mar; 28(5):. doi: 10.3390/molecules28052404. [PMID: 36903647]
  • Esmaeil Rezaei-Chiyaneh, Hassan Mahdavikia, Hadi Alipour, Aria Dolatabadian, Martin Leonardo Battaglia, Sagar Maitra, Matthew Tom Harrison. Biostimulants alleviate water deficit stress and enhance essential oil productivity: a case study with savory. Scientific reports. 2023 Jan; 13(1):720. doi: 10.1038/s41598-022-27338-w. [PMID: 36639680]
  • Rizan Elyasi, Mohammad Majdi, Sandra T Krause, Nagihan Kücükay, Abdolbaset Azizi, Jörg Degenhardt. Identification and functional characterization of a γ-terpinene synthase in Nigella sativa L (black cumin). Phytochemistry. 2022 Oct; 202(?):113290. doi: 10.1016/j.phytochem.2022.113290. [PMID: 35803303]
  • Mahdieh Modareskia, Mohammad Fattahi, Mohammad Hossein Mirjalili. Thymol screening, phenolic contents, antioxidant and antibacterial activities of Iranian populations of Trachyspermum ammi (L.) Sprague (Apiaceae). Scientific reports. 2022 Sep; 12(1):15645. doi: 10.1038/s41598-022-19594-7. [PMID: 36123425]
  • Zahra Dehghani-Aghchekohal, Mansoor Omidi, Reza Azizinezhad, Alireza Etminan. Stimulation of Secondary Metabolites and γ-Terpinene Synthase by Silver Nanoparticles in Callus Cultures of Carum carvi. Applied biochemistry and biotechnology. 2022 Jul; 194(7):3228-3241. doi: 10.1007/s12010-022-03879-8. [PMID: 35349082]
  • Nawaf Al-Maharik, Nidal Jaradat. Phytochemical Profile, Antimicrobial, Cytotoxic, and Antioxidant Activities of Fresh and Air-Dried Satureja nabateorum Essential Oils. Molecules (Basel, Switzerland). 2021 Dec; 27(1):. doi: 10.3390/molecules27010125. [PMID: 35011355]
  • Salman S Alharthi, Ahmed Noah Badr, Karolina Gromadzka, Kinga Stuper-Szablewska, Adel Gabr Abdel-Razek, Khaled Selim. Bioactive Molecules of Mandarin Seed Oils Diminish Mycotoxin and the Existence of Fungi. Molecules (Basel, Switzerland). 2021 Nov; 26(23):. doi: 10.3390/molecules26237130. [PMID: 34885712]
  • Luminita Capatina, Edoardo Marco Napoli, Giuseppe Ruberto, Lucian Hritcu. Origanum vulgare ssp. hirtum (Lamiaceae) Essential Oil Prevents Behavioral and Oxidative Stress Changes in the Scopolamine Zebrafish Model. Molecules (Basel, Switzerland). 2021 Nov; 26(23):. doi: 10.3390/molecules26237085. [PMID: 34885665]
  • María Constanza Luciardi, María Amparo Blázquez, María Rosa Alberto, Elena Cartagena, Mario Eduardo Arena. Lemon Oils Attenuate the Pathogenicity of Pseudomonas aeruginosa by Quorum Sensing Inhibition. Molecules (Basel, Switzerland). 2021 May; 26(10):. doi: 10.3390/molecules26102863. [PMID: 34066034]
  • Lamia Kerbouche, Mohamed Hazzit, Aoumeur Baaliouamer, Soraya Akretche. Distillation time effecting on the composition of Origanum floribundum essential oils and their antioxidant and antimicrobial activities. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2021 Mar; 76(3-4):153-160. doi: 10.1515/znc-2020-0102. [PMID: 33001858]
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  • Ghader Ghasemi, Abolfazl Alirezalu, Youbert Ghosta, Azadeh Jarrahi, Seyed Ali Safavi, Mahdi Abbas-Mohammadi, Francisco J Barba, Paulo E S Munekata, Rubén Domínguez, José M Lorenzo. Composition, Antifungal, Phytotoxic, and Insecticidal Activities of Thymus kotschyanus Essential Oil. Molecules (Basel, Switzerland). 2020 Mar; 25(5):. doi: 10.3390/molecules25051152. [PMID: 32143475]
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  • Mahdieh Eftekhari, Afsaneh Hoseinsalari, Mahboubeh Mansourian, Fatemeh Farjadmand, Mohammad Reza Shams Ardekani, Mohammad Sharifzadeh, Gholamreza Hassanzadeh, Mahnaz Khanavi, Mahdi Gholami. Trachyspermum ammi (L.) Sprague, superb essential oil and its major components on peptic ulcers: in vivo combined in silico studies. Daru : journal of Faculty of Pharmacy, Tehran University of Medical Sciences. 2019 Jun; 27(1):317-327. doi: 10.1007/s40199-019-00279-y. [PMID: 31218527]
  • Asit Ray, Sudipta Jena, Basudeba Kar, Jeetendranath Patnaik, Pratap Chandra Panda, Sanghamitra Nayak. Chemical composition and antioxidant activities of essential oil of Hedychium greenii and Hedychium gracile from India. Natural product research. 2019 May; 33(10):1482-1485. doi: 10.1080/14786419.2017.1416384. [PMID: 29252004]
  • Patricia R Quiroga, Valeria Nepote, María T Baumgartner. Contribution of organic acids to α-terpinene antioxidant activity. Food chemistry. 2019 Mar; 277(?):267-272. doi: 10.1016/j.foodchem.2018.10.100. [PMID: 30502144]
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