alpha-Terpineol acetate (BioDeep_00000396909)

human metabolite PANOMIX_OTCML-2023 Endogenous Volatile Flavor Compounds

代谢物信息卡片

(+/-)-alpha-Terpinyl acetate, predominantly alpha-isomer, technical, >=90\\% (GC)

化学式: C12H20O2 (196.14632200000003)
中文名称: 乙酸松油酯, 醋酸α-萜品酯, 萜品醇乙酸酯
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 0.49%

分子结构信息

SMILES: C1C(=CCC(C1)C(OC(C)=O)(C)C)C
InChI: InChI=1S/C12H20O2/c1-9-5-7-11(8-6-9)12(3,4)14-10(2)13/h5,11H,6-8H2,1-4H3

描述信息

alpha-Terpineol acetate, also known as a-terpineol acetic acid or p-menth-1-en-8-yl acetate, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. alpha-Terpineol acetate is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Alpha-Terpinyl acetate is a p-menthane monoterpenoid.
alpha-Terpinyl acetate is a natural product found in Xylopia sericea, Elettaria cardamomum, and other organisms with data available.
Terpinyl acetate is a metabolite found in or produced by Saccharomyces cerevisiae.
α-Terpinyl acetate is a monoterpene ester isolated from Laurus nobilis L. essential oil. α-Terpinyl acetate is a competitive P450 2B6 substrate which binding to the active site of P450 2B6 with a Kd value of 5.4?μM[1][2].
α-Terpinyl acetate is a monoterpene ester isolated from Laurus nobilis L. essential oil. α-Terpinyl acetate is a competitive P450 2B6 substrate which binding to the active site of P450 2B6 with a Kd value of 5.4?μM[1][2].

同义名列表

66 个代谢物同义名

(+/-)-alpha-Terpinyl acetate, predominantly alpha-isomer, technical, >=90\\% (GC); (+/-)-alpha-Terpinyl acetate, predominantly alpha-isomer, analytical standard; 3-Cyclohexene-1-methanol, .alpha.,.alpha.,4-trimethyl-, acetate, (1S)-; 3-Cyclohexene-1-methanol, .alpha.,.alpha.,4-trimethyl-, acetate, (1R)-; 3-Cyclohexene-1-methanol, .alpha.,.alpha.,4-trimethyl-, 1-acetate; 3-Cyclohexene-1-methanol, .alpha.,.alpha.,4-trimethyl-, acetate; 3-Cyclohexene-1-methanol, alpha,alpha,4-trimethyl-, 1-acetate; 3-Cyclohexene-1-methanol, alpha,alpha,4-trimethyl-, acetate; (1)-alpha,alpha,4-Trimethylcyclohex-3-ene-1-methyl acetate; .ALPHA.,.ALPHA.,4-TRIMETHYL-3-CYCLOHEXENE-1-METHYL ACETATE; alpha,alpha,4-Trimethyl-3-cyclohexene-1-methyl acetate; 1-Methyl-1-(4-methyl-3-cyclohexen-1-yl)ethyl acetate #; [1-methyl-1-(4-methylcyclohex-3-en-1-yl)ethyl] acetate; 1-methyl-1-(4-methylcyclohex-3-en-1-yl)ethyl acetate; (+/-)-2-(4-Methyl-3-cyclohexenyl)isopropyl acetate; 2-(4-methylcyclohex-3-en-1-yl)propan-2-yl acetate; 2-(4-methyl-1-cyclohex-3-enyl)propan-2-yl acetate; 2-(4-METHYL-3-CYCLOHEXEN-1-YL)-2-PROPYL ACETATE; 2-(4-methylcyclohex-3-enyl)propan-2-yl acetate; 4-06-00-00253 (Beilstein Handbook Reference); alpha-Terpinyl acetate, >=95\\%, FG; .ALPHA.-TERPINYL ACETATE. (+/-)-; .ALPHA.-TERPINYL ACETATE, (+/-)-; alpha-Terpinyl acetate, (+/-)-; p-Menth-1-en-8-yl acetic acid; (+/-)-alpha-Terpinyl acetate; IGODOXYLBBXFDW-UHFFFAOYSA-N; alpha-Terpineol acetic acid; .ALPHA.-TERPINEOL, ACETATE; p-Menth-1-en-8-ol, acetate; alpha-Terpinyl acetic acid; Terpinyl acetate (natural); .alpha.-Terpineol acetate; p-Menth-1-en-8-yl acetate; alpha-Terpineol, acetate; .alpha.-Terpinyl acetate; Α-terpineol acetic acid; alpha-Terpineol acetate; a-Terpineol acetic acid; Terpinyl acetate; >85\\%; a-Terpinyl acetic acid; Α-terpinyl acetic acid; alpha-Terpinyl acetate; α-Terpinyl acetate; a-Terpineol acetate; Α-terpineol acetate; a-?Terpinyl acetate; a-Terpinyl acetate; α-Terpinyl acetate; terpinenyl acetate; Terpineol, acetate; Terpineol acetate; terpinyl acetate; -erpinyl acetate; UNII-NIT9SZT3D7; UNII-9RXE0I9F2J; Tox21_303242; Tox21_202188; CAS-80-26-2; 9RXE0I9F2J; NIT9SZT3D7; AI3-00522; FEMA 3047; α-?Terpinyl acetate; alpha-Terpinyl acetate; alpha-Terpinyl acetate

数据库引用编号

20 个数据库交叉引用编号

ChEBI: CHEBI:32320
KEGG: C12300
PubChem: 111037
HMDB: HMDB0032051
DrugBank: DB15957
ChEMBL: CHEMBL3183581
LipidMAPS: LMPR0102090045
MeSH: terpinyl acetate
ChemIDplus: 0000080262
KNApSAcK: C00035043
foodb: FDB021665
chemspider: 99681
CAS: 10581-37-0
CAS: 8007-35-0
CAS: 80-26-2
medchemexpress: HY-N7136
PubChem: 582691
3DMET: B05625
NIKKAJI: J1.301C
KNApSAcK: 32320

分类词条

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)

42 个相关的物种来源信息

78264 - Abies sachalinensis: 10.1016/S0031-9422(00)94990-2
72329 - Artemisia herba-alba: 10.1016/S0031-9422(00)81692-1
466060 - Artemisia salsoloides: 10.1002/FFJ.2730070603
1643497 - Asarum asperum var. geaster: 10.1248/YAKUSHI1947.107.3_209
76089 - Asarum epigynum: 10.1248/YAKUSHI1947.107.3_209
76103 - Asarum hatsushimae: 10.1248/YAKUSHI1947.107.3_209
99808 - Chamaecyparis pisifera: 10.1016/S0031-9422(00)81063-8
2706 - Citrus: 10.1080/10412905.1993.9698179
3369 - Cryptomeria japonica: 10.1080/10412905.1991.9697930
105181 - Elettaria cardamomum: 10.1021/JF00011A018
1793945 - Eremophila serrulata: 10.1248/CPB.24.56
3932 - Eucalyptus: 10.4324/9780203219430_CHAPTER_13
34316 - Eucalyptus camaldulensis: 10.1080/10412905.1991.9697921
380073 - Heracleum dissectum: 10.1055/S-2007-969171
9606 - Homo sapiens: -
128638 - Licaria triandra: 10.1007/BF02985250
88853 - Litsea glaucescens: 10.1007/BF02985250
164936 - Melaleuca leucadendra: 10.1002/CBDV.200900162
164958 - Melaleuca uncinata: 10.1002/CBDV.200900162
292239 - Mentha arvensis: 10.1016/J.PHYTOCHEM.2006.04.025
54731 - Nepeta racemosa: 10.1080/10412905.1993.9698205
48386 - Perilla frutescens: 10.1021/JF00023A054
130377 - Piper aduncum: 10.1055/S-2006-957911
405316 - Piper aequale: 10.1016/J.PHYTOCHEM.2006.04.025
33090 - Plants: -
58046 - Platycladus orientalis: 10.1076/PHBI.39.5.388.5894
184183 - Primula hirsuta: 10.1248/CPB.24.2470
313948 - Rhanterium epapposum: 10.1002/FFJ.2730020106
268906 - Salvia fruticosa: 10.1016/S0367-326X(01)00327-6
169606 - Tagetes lucida: 10.1002/(SICI)1099-1026(199701)12:1<47::AID-FFJ610>3.0.CO;2-7
1209841 - Teucrium asiaticum: 10.1016/0031-9422(90)85421-B
1209881 - Teucrium oxylepis: 10.1016/0031-9422(90)85421-B
1209889 - Teucrium salviastrum: 10.1016/0031-9422(90)85421-B
53178 - Teucrium scorodonia: 10.1016/0031-9422(90)85421-B
1194133 - Thymus longicaulis: 10.1080/10412905.1993.9698222
945837 - Vaccinium ashei: 10.1111/J.1365-2621.1985.TB13419.X
69266 - Vaccinium corymbosum: 10.1111/J.1365-2621.1985.TB13419.X
1493660 - Vaccinium virgatum: 10.1111/J.1365-2621.1985.TB13419.X
54477 - Vitex agnus-castus: 10.1080/10412905.1990.9697840
204215 - Vitex trifolia: 10.1002/FFJ.2730060115
1005659 - Xylopia sericea: 10.1021/NP50048A039
94328 - Zingiber Officinale Roscoe: -

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

Bei Cui, Tao Zheng, Ping Deng, Sheng Zhang, Zhong Zhao. Chemotaxonomic Variation in Volatile Component Contents in Ancient Platycladus orientalis Leaves with Different Tree Ages in Huangdi Mausoleum. Molecules (Basel, Switzerland). 2023 Feb; 28(5):. doi: 10.3390/molecules28052043. [PMID: 36903288]
Shengnan Xu, Li Yu, Yuping Hou, Bo Huang, Hong Wang, Dengwu Li, Dongmei Wang. Chemical composition, chemotypic characterization, and histochemical localization of volatile components in different cultivars of Zanthoxylum bungeanum Maxim. leaves. Journal of food science. 2023 Feb; ?(?):. doi: 10.1111/1750-3841.16490. [PMID: 36786362]
Vaida Vaičiulytė, Kristina Ložienė, Jurgita Švedienė, Vita Raudonienė, Algimantas Paškevičius. α-Terpinyl Acetate: Occurrence in Essential Oils Bearing Thymus pulegioides, Phytotoxicity, and Antimicrobial Effects. Molecules (Basel, Switzerland). 2021 Feb; 26(4):. doi: 10.3390/molecules26041065. [PMID: 33670506]
Shehar Bano, Azeem Intisar, Mahd Rauf, Abdul Ghaffar, Farhat Yasmeen, Waheed-Uz- Zaman, Uzma Intisar, Gulnaz Kausar, Nadeem Muhammad, Aqsa Aamir. Comparative analysis of oil composition and antibacterial activity of aerial parts of Terminalia arjuna (Roxb.). Natural product research. 2020 May; 34(9):1311-1314. doi: 10.1080/14786419.2018.1557656. [PMID: 30618269]
Arielle J Johnson, Anna K Hjelmeland, Hildegarde Heymann, Susan E Ebeler. GC-Recomposition-Olfactometry (GC-R) and multivariate study of three terpenoid compounds in the aroma profile of Angostura bitters. Scientific reports. 2019 05; 9(1):7633. doi: 10.1038/s41598-019-44064-y. [PMID: 31113980]
Nawroz Abdul-Razzak Tahir, Hoshyar Abdullah Azeez, Kadhm Abdullah Muhammad, Shewa Anwer Faqe, Dlshad Ali Omer. Exploring of bioactive compounds in essential oil acquired from the stem and root derivatives of Hypericum triquetrifolium callus cultures. Natural product research. 2019 May; 33(10):1504-1508. doi: 10.1080/14786419.2017.1419228. [PMID: 29277112]
Wanping Zhu, Xia Liu, Yuji Wang, Yeling Tong, Yongzhou Hu. Discovery of a novel series of α-terpineol derivatives as promising anti-asthmatic agents: Their design, synthesis, and biological evaluation. European journal of medicinal chemistry. 2018 Jan; 143(?):419-425. doi: 10.1016/j.ejmech.2017.07.068. [PMID: 29202404]
Kamiar Zomorodian, Mahmoodreza Moein, Keyvan Pakshir, Forough Karami, Zahra Sabahi. Chemical Composition and Antimicrobial Activities of the Essential Oil From Salvia mirzayanii Leaves. Journal of evidence-based complementary & alternative medicine. 2017 10; 22(4):770-776. doi: 10.1177/2156587217717414. [PMID: 28689440]
Gordana Stojanović, Olga Jovanović, Goran Petrović, Violeta Mitić, Vesna Stankov Jovanović, Snežana Jovanović. Composition of headspace volatiles and essential oils of three Thymus species. Natural product communications. 2014 Nov; 9(11):1609-12. doi: . [PMID: 25532293]
Rajendra C Padalia, Ram S Verma, Amit Chauhan, Chandan S Chanotiya. Chemical composition of leaf and root essential oils of Boenninghausenia albiflora Reichb. from northern India. Natural product research. 2012 Nov; 26(21):2040-4. doi: 10.1080/14786419.2011.635344. [PMID: 22111591]
Mohammad Moradi, Massoud Kaykhaii, Ali Reza Ghiasvand, Shahriar Shadabi, Alinazar Salehinia. Comparison of headspace solid-phase microextraction, headspace single-drop microextraction and hydrodistillation for chemical screening of volatiles in Myrtus communis L. Phytochemical analysis : PCA. 2012 Jul; 23(4):379-86. doi: 10.1002/pca.1368. [PMID: 22069217]
Hanen Marzouki, Abdelhamid Khaldi, Bruno Marongiu, Alessandra Piras, Fethia Harzallah-Skhiri. Chemical polymorphism of essential oils from populations of Laurus nobilis grown on Tunisia, Algeria and France. Natural product communications. 2011 Oct; 6(10):1483-6. doi: ". [PMID: 22164789]
Ying-Ju Chen, Chun-Ya Lin, Seng-Sung Cheng, Shang-Tzen Chang. Phylogenetic relationships of the genus Chamaecyparis inferred from leaf essential oil. Chemistry & biodiversity. 2011 Jun; 8(6):1083-97. doi: 10.1002/cbdv.201000348. [PMID: 21674781]
Habib Abbasipour, Mohammad Mahmoudvand, Fahimeh Rastegar, Mohammad Hossein Hosseinpour. Fumigant toxicity and oviposition deterrency of the essential oil from cardamom, Elettaria cardamomum, against three stored–product insects. Journal of insect science (Online). 2011; 11(?):165. doi: 10.1673/031.011.16501. [PMID: 22242564]
Birgul Ozcan, Mari Esen, M Kemal Sangun, Arzu Coleri, Mahmut Caliskan. Effective antibacterial and antioxidant properties of methanolic extract of Laurus nobilis seed oil. Journal of environmental biology. 2010 Sep; 31(5):637-41. doi: ". [PMID: 21387914]
Ali Shafaghat. Free radical scavenging and antibacterial activities, and GC/MS analysis of essential oils from different parts of Falcaria vulgaris from two regions. Natural product communications. 2010 Jun; 5(6):981-4. doi: . [PMID: 20614839]
Hayet Edziri, Maha Mastouri, Imed Cheraif, Mahjoub Aouni. Chemical composition and antibacterial, antifungal and antioxidant activities of the flower oil of Retama raetam (Forssk.) Webb from Tunisia. Natural product research. 2010 May; 24(9):789-96. doi: 10.1080/14786410802529190. [PMID: 20461625]
Bruno Marongiu, Alessandra Piras, Silvia Porcedda, Danilo Falconieri, Maria J Goncalves, Ligia Salgueiro, Andrea Maxia, Roberta Lai. Extraction, separation and isolation of volatiles from Vitex agnus-castus L. (Verbenaceae) wild species of Sardinia, Italy, by supercritical CO2. Natural product research. 2010 Apr; 24(6):569-79. doi: 10.1080/14786410902899915. [PMID: 20397107]
Yinzhe Jin, Dandan Han, Minglei Tian, Kyung-Ho Row. Supercritical CO2 extraction of essential oils from Chamaecyparis obtusa. Natural product communications. 2010 Mar; 5(3):461-4. doi: ". [PMID: 20420328]
Cengiz Sarikurkcu, Kadir Arisoy, Bektas Tepe, Ahmet Cakir, Gulsah Abali, Ebru Mete. Studies on the antioxidant activity of essential oil and different solvent extracts of Vitexagnuscastus L. fruits from Turkey. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2009 Oct; 47(10):2479-83. doi: 10.1016/j.fct.2009.07.005. [PMID: 19595732]
Moses S Owolabi, Labunmi Lajide, Matthew O Oladimeji, William N Setzer, Maria C Palazzo, Rasaq A Olowu, Akintayo Ogundajo. Volatile constituents and antibacterial screening of the essential oil of Chenopodium ambrosioides L. growing in Nigeria. Natural product communications. 2009 Jul; 4(7):989-92. doi: . [PMID: 19731609]
Marina D Soković, Jelena Vukojević, Petar D Marin, Dejan D Brkić, Vlatka Vajs, Leo J L D van Griensven. Chemical composition of essential oils of Thymus and Mentha species and their antifungal activities. Molecules (Basel, Switzerland). 2009 Jan; 14(1):238-49. doi: 10.3390/molecules14010238. [PMID: 19136911]
Hanen Marzouki, Abdelhamid Khaldi, Rachid Chamli, Sadok Bouzid, Alessandra Piras, Danilo Falconieri, Bruno Marongiu. Biological activity evaluation of the oils from Laurus nobilis of Tunisia and Algeria extracted by supercritical carbon dioxide. Natural product research. 2009; 23(3):230-7. doi: 10.1080/14786410801976400. [PMID: 19235023]
H Marzouki, A Piras, K Bel Haj Salah, H Medini, T Pivetta, S Bouzid, B Marongiu, D Falconieri. Essential oil composition and variability of Laurus nobilis L. growing in Tunisia, comparison and chemometric investigation of different plant organs. Natural product research. 2009; 23(4):343-54. doi: 10.1080/14786410802076200. [PMID: 19296375]
Alam Khan, Goher Zaman, Richard A Anderson. Bay leaves improve glucose and lipid profile of people with type 2 diabetes. Journal of clinical biochemistry and nutrition. 2009 Jan; 44(1):52-6. doi: 10.3164/jcbn.08-188. [PMID: 19177188]
Mohammadreza Verdian-rizi, Abbas Hadjiakhoondi. Essential oil composition of Laurus nobilis L. of different growth stages growing in Iran. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2008 Nov; 63(11-12):785-8. doi: 10.1515/znc-2008-11-1201. [PMID: 19227823]
Hanen Marzouki, Alessandra Piras, Bruno Marongiu, Antonella Rosa, M Assunta Dessì. Extraction and separation of volatile and fixed oils from berries of Laurus nobilis L. by Supercritical CO2. Molecules (Basel, Switzerland). 2008 Aug; 13(8):1702-11. doi: 10.3390/molecules13081702. [PMID: 18794780]
Biljana Nikolić, Mihailo Ristić, Srdjan Bojović, Petar D Marin. Variability of the needle essential oils of Pinus peuce from different populations in Montenegro and Serbia. Chemistry & biodiversity. 2008 Jul; 5(7):1377-88. doi: 10.1002/cbdv.200890126. [PMID: 18649304]
Sanjay Guleria, Ashok Kumar, Ashok Kumar Tiku. Chemical composition and fungitoxic activity of essential oil of Thuja orientalis L. grown in the north-western Himalaya. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2008 Mar; 63(3-4):211-4. doi: 10.1515/znc-2008-3-409. [PMID: 18533464]
Jeong-Dan Cha, Eun-Kyung Jung, Bong-Seop Kil, Kyung-Yeol Lee. Chemical composition and antibacterial activity of essential oil from Artemisia feddei. Journal of microbiology and biotechnology. 2007 Dec; 17(12):2061-5. doi: . [PMID: 18167456]
Hasan Yalçin, Mehtap Anik, Murat Aydin Sanda, Ahmet Cakir. Gas chromatography/mass spectrometry analysis of Laurus nobilis essential oil composition of northern Cyprus. Journal of medicinal food. 2007 Dec; 10(4):715-9. doi: 10.1089/jmf.2007.404. [PMID: 18158847]
Mustafa Kemal Sangun, Ebru Aydin, Mahir Timur, Hatice Karadeniz, Mahmut Caliskan, Aydin Ozkan. Comparison of chemical composition of the essential oil of Laurus nobilis L. leaves and fruits from different regions of Hatay, Turkey. Journal of environmental biology. 2007 Oct; 28(4):731-3. doi: ". [PMID: 18405104]
Jae-Kyung Yang, Myung-Suk Choi, Weon-Taek Seo, Danny Lee Rinker, Sang Woo Han, Gang-Won Cheong. Chemical composition and antimicrobial activity of Chamaecyparis obtusa leaf essential oil. Fitoterapia. 2007 Feb; 78(2):149-52. doi: 10.1016/j.fitote.2006.09.026. [PMID: 17161919]
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Alessandra Caredda, Bruno Marongiu, Silvia Porcedda, Carla Soro. Supercritical carbon dioxide extraction and characterization of Laurus nobilis essential oil. Journal of agricultural and food chemistry. 2002 Mar; 50(6):1492-6. doi: 10.1021/jf0108563. [PMID: 11879026]
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J Yamahara, H Kimura, M Kobayashi, T Sawada, H Fujimura, T Chisaka. [Biologically active principles of crude drugs. Cholagogic substances in cardamon seed and their properties]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 1983 Sep; 103(9):979-85. doi: 10.1248/yakushi1947.103.9_979. [PMID: 6674494]