Benzyl benzoate (BioDeep_00000003745)

 

Secondary id: BioDeep_00000406361, BioDeep_00000861942

human metabolite PANOMIX_OTCML-2023 blood metabolite


代谢物信息卡片


Benzyl benzoate, Pharmaceutical Secondary Standard; Certified Reference Material

化学式: C14H12O2 (212.0837252)
中文名称: 苯甲酸苄酯
谱图信息: 最多检出来源 Homo sapiens(blood) 0.55%

分子结构信息

SMILES: C1=CC=C(C=C1)COC(=O)C2=CC=CC=C2
InChI: InChI=1S/C14H12O2/c15-14(13-9-5-2-6-10-13)16-11-12-7-3-1-4-8-12/h1-10H,11H2

描述信息

Benzyl benzoate, also known as benylate or benylic acid, belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Benzyl benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa). Benzyl benzoate is a faint, sweet, and almond tasting compound. Outside of the human body, benzyl benzoate is found, on average, in the highest concentration within Ceylon cinnamon. Benzyl benzoate has also been detected, but not quantified in, several different foods, such as fennels, garden tomato, annual wild rice, amaranths, and horseradish tree. This could make benzyl benzoate a potential biomarker for the consumption of these foods. Benzyl benzoate is one of the older preparations used to treat scabies. Scabies is a skin infection caused by the mite Sarcoptes scabiei. It is characterized by severe itching (particularly at night), red spots, and may lead to a secondary infection. Benzyl benzoate is lethal to this mite and is therefore useful in the treatment of scabies. It is also used to treat lice infestations of the head and body.
Benzyl benzoate is a benzoate ester obtained by the formal condensation of benzoic acid with benzyl alcohol. It has been isolated from the plant species of the genus Polyalthia. It has a role as a scabicide, an acaricide and a plant metabolite. It is a benzyl ester and a benzoate ester. It is functionally related to a benzoic acid.
Benzyl benzoate is one of the older preparations used to treat scabies. Scabies is a skin infection caused by the mite sarcoptes scabiei. It is characterised by severe itching (particularly at night), red spots, and may lead to a secondary infection. Benzyl benzoate is lethal to this mite and so is useful in the treatment of scabies. It is also used to treat lice infestation of the head and body. Benzyl benzoate is not the treatment of choice for scabies due to its irritant properties.
Benzyl benzoate is a natural product found in Lonicera japonica, Populus tremula, and other organisms with data available.
See also: ... View More ...
P - Antiparasitic products, insecticides and repellents > P03 - Ectoparasiticides, incl. scabicides, insecticides and repellents > P03A - Ectoparasiticides, incl. scabicides
A benzoate ester obtained by the formal condensation of benzoic acid with benzyl alcohol. It has been isolated from the plant species of the genus Polyalthia.
Contained in Peru balsam and Tolu balsam. Isolated from other plants e.g. Jasminum subspecies, ylang-ylang oil. It is used in food flavouring
C254 - Anti-Infective Agent > C276 - Antiparasitic Agent
D010575 - Pesticides > D007306 - Insecticides
D016573 - Agrochemicals
Same as: D01138
Benzyl benzoate (Benzoic acid benzyl ester) is a fragrance ingredient in cosmetic products. Benzyl benzoate can be used for the research of Scabies and Demodex-associated inflammatory skin conditions[1][2][3].
Benzyl benzoate (Phenylmethyl benzoate) is an orally active anti-scabies agent, acaricide (EC50= 0.06 g/m2) and fungicide. Benzyl benzoate is an angiotensin II (Ang II) inhibitor with antihypertensive effects. Benzyl benzoate can be used in perfumes, pharmaceuticals and the food industry[1][2][3][4][5].
Benzyl benzoate (Benzoic acid benzyl ester) is a fragrance ingredient in cosmetic products. Benzyl benzoate can be used for the research of Scabies and Demodex-associated inflammatory skin conditions[1][2][3].

同义名列表

123 个代谢物同义名

Benzyl benzoate, Pharmaceutical Secondary Standard; Certified Reference Material; InChI=1/C14H12O2/c15-14(13-9-5-2-6-10-13)16-11-12-7-3-1-4-8-12/h1-10H,11H; Benzyl benzoate, United States Pharmacopeia (USP) Reference Standard; Benzyl benzoate, certified reference material, TraceCERT(R); Benzoic acid benzyl ester; Benzoic acid phenylmethyl ester; Benzyl benzoate, meets USP testing specifications; Benzyl benzoate, Vetec(TM) reagent grade, 98\\%; 4-09-00-00307 (Beilstein Handbook Reference); Benzyl benzoate, SAJ special grade, >=99.0\\%; Benzyl benzoate, tested according to Ph.Eur.; Benzyl benzoate, SAJ first grade, >=98.0\\%; Benzyl benzoate, natural, >=99\\%, FCC, FG; Benzyl benzoate, ReagentPlus(R), >=99.0\\%; Benzyl benzoate, for synthesis, 99.0\\%; Benzylester kyseliny benzoove [Czech]; Benzyl benzoate, analytical standard; Benzyl benzoate, >=99\\%, FCC, FG; Benzoic acid, phenylmethyl ester; BENZYL BENZOATE [USP MONOGRAPH]; BENZYLIS BENZOAS [WHO-IP LATIN]; BENZYL BENZOATE (USP MONOGRAPH); BENZYL BENZOATE [EP MONOGRAPH]; BENZYL BENZOATE (USP IMPURITY); BENZYL BENZOATE (EP MONOGRAPH); BENZYL BENZOATE [USP IMPURITY]; BENZOIC ACID PHENYLMETHYLESTER; Benzylester kyseliny benzoove; BENZYL BENZOATE (EP IMPURITY); BENZYL BENZOATE [ORANGE BOOK]; BENZYL BENZOATE [EP IMPURITY]; Benzyl alcohol benzoic ester; Benzoate, phenylmethyl ester; Benzylbenzoaat Smeersel FNA; Benzyl benzoate (JP17/USP); Benzoic acid, benzyl ester; BENZOate phenylmethylester; Benzyl benzenecarboxylate; BENZOIC ACID,BENZYL ESTER; Phenylmethyl benzoic acid; Benzoic acid-benzyl ester; Benzoic acid benzyl ester; Benzyl benzoate (USP:JAN); Benzyl benzoate (natural); Benzyl benzoate [USP:JAN]; BENZYL BENZOATE [USP-RS]; BENZYL BENZOATE [WHO-DD]; BENZYL BENZOATE (USP-RS); Benzylbenzenecarboxylate; BENZYL BENZOATE [WHO-IP]; BENZYL BENZOATE (MART.); BENZYLOXY PHENYL KETONE; Benzyl benzoate, >=99\\%; BENZYL BENZOATE [MART.]; Benzoesaeurebenzylester; Benzoate, benzyl ester; BENZYL BENZOATE [HSDB]; Benzoesaurebenzylester; BENZYL BENZOATE [FHFI]; BENZYL BENZOATE [INCI]; Phenylmethyl benzoate; BENZYL BENZOATE [FCC]; BENZYL BENZOATE [JAN]; BENZYL BENZOATE [MI]; BENZYL BENZOATE [II]; Benzyl phenylformate; BENZYL BENZOATE (II); Benzoate de benzyle; Benzyl benzoic acid; BENZYL-D5 BENZOATE; Benzylum benzoicum; Spectrum4_000773; Benzylis benzoas; Spectrum3_001757; Spectrum5_001128; Spectrum2_000532; benzyl-benzoate; Benzyl Benzoate; benzylbenzoate; Benzyl benzoat; Tox21_111372_1; Antiscabiosum; DivK1c_000204; Benylate (TN); Benylic acid; KBio2_004288; Tox21_111372; KBio1_000204; Tox21_303418; KBio3_002714; Tox21_201337; KBio2_001720; KBio2_006856; IDI1_000204; Peruscabina; Acarobenzyl; Novoscabin; WLN: RVO1R; Peruscabin; Benzylets; Venzonate; Scabiozon; AI3-00523; Acarosan; Benzanil; Scabitox; Scabagen; Ascabiol; Colebenz; Benzemul; Benzevan; Scobenol; Venzoate; Scabanca; Vanzoate; Benylate; Scabide; Ascabin; Acaril; Bengal; Benzyl; Ansar; 1dzm; BZM



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(0)

BioCyc(4)

PlantCyc(0)

代谢反应

44 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(6)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(38)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

141 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

  • Zheng Chen, Mei-Zhu Wu, Ting Zheng, Ya-Lin Chen, Chen Sun, Yong-Hao Lou, Xue-Ming Zhou. [Two new benzyl-benzoate glucosides from Plumeria rubra]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2024 Mar; 49(5):1255-1259. doi: 10.19540/j.cnki.cjcmm.20231209.202. [PMID: 38621972]
  • Ty Viet Pham, Nguyen Xuan Ha, Nguyen Dinh Luyen, Thao Hoang Xuan, Thang Le Quoc, Nguyen Huy Hung, Ninh The Son. Chemical Composition, Mosquito Larvicidal and Antimicrobial Activities, and Molecular Docking Study of Essential Oils of Cinnamomum melastomaceum , Neolitsea buisanensis  and Uvaria microcarpa from Vietnam. Chemistry & biodiversity. 2023 Aug; ?(?):e202300652. doi: 10.1002/cbdv.202300652. [PMID: 37531297]
  • Young Sang Kwon, Chang-Beom Park, Seung-Min Lee, Seonggeun Zee, Go-Eun Kim, Yeong-Jin Kim, Hee-Jung Sim, Jong-Hwan Kim, Jong-Su Seo. Proteomic analysis of zebrafish (Danio rerio) embryos exposed to benzyl benzoate. Environmental science and pollution research international. 2022 Nov; ?(?):. doi: 10.1007/s11356-022-24081-7. [PMID: 36367642]
  • Aysun Kılıç Süloğlu, Evrim A Koçkaya, Güldeniz Selmanoğlu. Toxicity of benzyl benzoate as a food additive and pharmaceutical agent. Toxicology and industrial health. 2022 Apr; 38(4):221-233. doi: 10.1177/07482337221086133. [PMID: 35332820]
  • Joannna Igielska-Kalwat, Slawa Połoczańska-Godek, Ewa Kilian-Pięta. The use of Dalmatian pyrethrum daisy and an excipient in the treatment of seborrheic dermatitis. Acta biochimica Polonica. 2022 Feb; 69(1):123-129. doi: 10.18388/abp.2020_5770. [PMID: 35225498]
  • Seon-Mi Seo, Jae-Woo Lee, Jonghyun Shin, Jun-Hyung Tak, Jinho Hyun, Il-Kwon Park. Development of cellulose nanocrystal-stabilized Pickering emulsions of massoia and nutmeg essential oils for the control of Aedes albopictus. Scientific reports. 2021 06; 11(1):12038. doi: 10.1038/s41598-021-91442-6. [PMID: 34103581]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Gasper Maeda, Jelle van der Wal, Arvind Kumar Gupta, Joan J E Munissi, Andreas Orthaber, Per Sunnerhagen, Stephen S Nyandoro, Máté Erdélyi. Oxygenated Cyclohexene Derivatives and Other Constituents from the Roots of Monanthotaxis trichocarpa. Journal of natural products. 2020 02; 83(2):210-215. doi: 10.1021/acs.jnatprod.9b00363. [PMID: 31986029]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
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  • Nan Zhang, Lei Zhang, Linyin Feng, Lei Yao. The anxiolytic effect of essential oil of Cananga odorata exposure on mice and determination of its major active constituents. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2016 Dec; 23(14):1727-1734. doi: 10.1016/j.phymed.2016.10.017. [PMID: 27912874]
  • Gajanand Sharma, Geeta Dhankar, Kanika Thakur, Kaisar Raza, O P Katare. Benzyl Benzoate-Loaded Microemulsion for Topical Applications: Enhanced Dermatokinetic Profile and Better Delivery Promises. AAPS PharmSciTech. 2016 Oct; 17(5):1221-31. doi: 10.1208/s12249-015-0464-0. [PMID: 26669889]
  • Juliana Maria de Mello Andrade, Carolina Dos Santos Passos, Maria Angélica Kieling Rubio, Jacqueline Nakau Mendonça, Norberto Peporine Lopes, Amélia Teresinha Henriques. Combining in vitro and in silico approaches to evaluate the multifunctional profile of rosmarinic acid from Blechnum brasiliense on targets related to neurodegeneration. Chemico-biological interactions. 2016 Jul; 254(?):135-45. doi: 10.1016/j.cbi.2016.06.005. [PMID: 27270453]
  • Jun-Ran Kim, Haribalan Perumalsamy, Min Jung Kwon, Se Um Chae, Young-Joon Ahn. Toxicity of hiba oil constituents and spray formulations to American house dust mites and copra mites. Pest management science. 2015 May; 71(5):737-43. doi: 10.1002/ps.3843. [PMID: 24916027]
  • Russell J Chedgy, Tobias G Köllner, C Peter Constabel. Functional characterization of two acyltransferases from Populus trichocarpa capable of synthesizing benzyl benzoate and salicyl benzoate, potential intermediates in salicinoid phenolic glycoside biosynthesis. Phytochemistry. 2015 May; 113(?):149-59. doi: 10.1016/j.phytochem.2014.10.018. [PMID: 25561400]
  • Shanmugam Krishnamoorthy, Manivachagam Chandrasekaran, Gnanaprakasam Adaikala Raj, Mahalingam Jayaraman, Venugopalan Venkatesalu. Identification of chemical constituents and larvicidal activity of essential oil from Murraya exotica L. (Rutaceae) against Aedes aegypti, Anopheles stephensi and Culex quinquefasciatus (Diptera: Culicidae). Parasitology research. 2015 May; 114(5):1839-45. doi: 10.1007/s00436-015-4370-x. [PMID: 25697880]
  • Haribalan Perumalsamy, Jae Yeon Kim, Jun-Ran Kim, Kum Na Ra Hwang, Young-Joon Ahn. Toxicity of basil oil constituents and related compounds and the efficacy of spray formulations to Dermatophagoides farinae (Acari: Pyroglyphidae). Journal of medical entomology. 2014 May; 51(3):650-7. doi: 10.1603/me13235. [PMID: 24897858]
  • Kedar Rokade, Gajanan Mali. Biodegradation of benzyl benzoate by Pseudomonas desmolyticum NCIM 2112. World journal of microbiology & biotechnology. 2014 Mar; 30(3):827-33. doi: 10.1007/s11274-013-1484-0. [PMID: 24146308]
  • E Arzu Koçkaya, Aysun Kılıç. Developmental toxicity of benzyl benzoate in rats after maternal exposure throughout pregnancy. Environmental toxicology. 2014 Jan; 29(1):40-53. doi: 10.1002/tox.20771. [PMID: 21922633]
  • Le D Hieu, Tran D Thang, Tran M Hoi, Isiaka A Ogunwande. Chemical composition of essential oils from four Vietnamese species of piper (piperaceae). Journal of oleo science. 2014; 63(3):211-7. doi: 10.5650/jos.ess13175. [PMID: 24712088]
  • Namki Cho, Heejung Yang, Mina Lee, Jungmoo Huh, Hyeon-Woo Kim, Hong-Pyo Kim, Sang-Hyun Sung. Neuroprotective benzyl benzoate glycosides from Disporum viridescens roots in HT22 hippocampal neuronal cells. Journal of natural products. 2013 Dec; 76(12):2291-7. doi: 10.1021/np400676b. [PMID: 24246008]
  • Jeong-Oh Yang, Naoya Nakayama, Kyohei Toda, Shinichi Tebayashi, Chul-Sa Kim. Elicitor(s) in Sogatella furcifera (Horváth) causing the Japanese rice plant (Oryza sativa L.) to induce the ovicidal substance, benzyl benzoate. Bioscience, biotechnology, and biochemistry. 2013; 77(6):1258-61. doi: 10.1271/bbb.130055. [PMID: 23748769]
  • Lei Liu, Yuan-hui Guo, Hai-liang Xin, Yan Nie, Ting Han, Lu-ping Qin, Qiao-yan Zhang. Antiosteoporotic effects of benzyl benzoate glucosides from Curculigo orchioides in ovariectomized rats. Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine. 2012 Dec; 10(12):1419-26. doi: 10.3736/jcim20121214. [PMID: 23257136]
  • Sarah Miesner, Holly Frosch, Kelly Kindscher, Shane Tichy, Kirk P Manfredi. Benzyl benzoate glycosides from Oligoneuron rigidum. Journal of natural products. 2012 Nov; 75(11):1903-8. doi: 10.1021/np300379h. [PMID: 23121124]
  • Haiqiang Wu, Jing Li, Fang Zhang, Li Li, Zhigang Liu, Zhendan He. Essential oil components from Asarum sieboldii Miquel are toxic to the house dust mite Dermatophagoides farinae. Parasitology research. 2012 Nov; 111(5):1895-9. doi: 10.1007/s00436-012-3032-5. [PMID: 22833176]
  • Ju-Hyun Jeon, Ji-Yeon Yang, Hoi-Seon Lee. Acaricidal activities of materials derived from Pyrus ussuriensis fruits against stored food mites. Journal of food protection. 2012 Jul; 75(7):1258-62. doi: 10.4315/0362-028x.jfp-12-040. [PMID: 22980009]
  • Yeon-Kyeong Yun, Hyun-Kyung Kim, Jun-Ran Kim, Kumnara Hwang, Young-Joon Ahn. Contact and fumigant toxicity of Armoracia rusticana essential oil, allyl isothiocyanate and related compounds to Dermatophagoides farinae. Pest management science. 2012 May; 68(5):788-94. doi: 10.1002/ps.2327. [PMID: 22102526]
  • Min Seok Oh, Ji-Yeon Yang, Hoi Seon Lee. Acaricidal toxicity of 2'-hydroxy-4'-methylacetophenone isolated from Angelicae koreana roots and structure-activity relationships of its derivatives. Journal of agricultural and food chemistry. 2012 Apr; 60(14):3606-11. doi: 10.1021/jf205379u. [PMID: 22429095]
  • Ken Shiraiwa, Shen Yuan, Ayako Fujiyama, Yosuke Matsuo, Takashi Tanaka, Zhi-Hong Jiang, Isao Kouno. Benzyl benzoate glycoside and 3-deoxy-D-manno-2-octulosonic acid derivatives from Solidago decurrens. Journal of natural products. 2012 Jan; 75(1):88-92. doi: 10.1021/np2007582. [PMID: 22185651]
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  • Yu Ling, Chunyu Zhang, Tong Chen, Huaiqing Hao, Peng Liu, Ray A Bressan, Paul M Hasegawa, Jing Bo Jin, Jinxing Lin. Mutation in SUMO E3 ligase, SIZ1, disrupts the mature female gametophyte in Arabidopsis. PloS one. 2012; 7(1):e29470. doi: 10.1371/journal.pone.0029470. [PMID: 22253727]
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  • Gajanan B Zore, Archana D Thakre, Sitaram Jadhav, S Mohan Karuppayil. Terpenoids inhibit Candida albicans growth by affecting membrane integrity and arrest of cell cycle. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2011 Oct; 18(13):1181-90. doi: 10.1016/j.phymed.2011.03.008. [PMID: 21596542]
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  • Ilaria D'Acquarica, Antonella Cerreto, Giuliano Delle Monache, Fabiana Subrizi, Alberto Boffi, Andrea Tafi, Stefano Forli, Bruno Botta. N-linked peptidoresorc[4]arene-based receptors as noncompetitive inhibitors for α-chymotrypsin. The Journal of organic chemistry. 2011 Jun; 76(11):4396-407. doi: 10.1021/jo102592f. [PMID: 21534559]
  • Karina Caballero-Gallardo, Jesús Olivero-Verbel, Elena E Stashenko. Repellent activity of essential oils and some of their individual constituents against Tribolium castaneum herbst. Journal of agricultural and food chemistry. 2011 Mar; 59(5):1690-6. doi: 10.1021/jf103937p. [PMID: 21291237]
  • Zhangqian Wang, Hyun-Kyung Kim, Wenqi Tao, Mo Wang, Young-Joon Ahn. Contact and fumigant toxicity of cinnamaldehyde and cinnamic acid and related compounds to Dermatophagoides farinae and Dermatophagoides pteronyssinus (Acari: Pyroglyphidae). Journal of medical entomology. 2011 Mar; 48(2):366-71. doi: 10.1603/me10127. [PMID: 21485375]
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