(4S,5R,8S,9R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-ol

Base Information

• Chemical Name: (4S,5R,8S,9R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-ol
• CAS No.: 71939-50-9
• Molecular Formula: C15H24O5
• Molecular Weight: 284.353
• Hs Code.: 29329990
• Metabolomics Workbench ID: 130140
• NCI Thesaurus Code: C87432
• Mol file: 71939-50-9.mol

Synonyms:(3R,5aS,6R,8aS,9R,10S,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10-ol;3alpha-hydroxydeoxydihydroartemisinin;8alpha-hydroxydeoxyartemisinin;9alpha-hydroxydeoxyartemisinin;Alaxin;artemisinin, dihydro-;artenimol;Cotecxin;Cotexin;dihydroartemisinin;dihydroartemisinine;dihydroqinghaosu;dihydroquinghaosu;dihydroquinghaosu, (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10alpha,12alpha,12aR*))-isomer;dihydroquinghaosu, (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10beta,12alpha,12aR*))-isomer;quinghaosu, dihydro-;Salaxin;Santecxin

Chemical Property of (4S,5R,8S,9R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-ol

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 3.52E-07mmHg at 25°C
• Melting Point: 144-149 °C
• Refractive Index: 1.542
• Boiling Point: 375.6 °C at 760 mmHg
• PKA: 12.61±0.70(Predicted)
• Flash Point: 181 °C
• PSA: 57.15000
• Density: 1.24 g/cm³
• LogP: 2.18670
• Storage Temp.: 2-8°C
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 284.16237386
• Heavy Atom Count: 20
• Complexity: 415

Purity/Quality:

99% ^*data from raw suppliers

DihydroArtemisinin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCC2C(C(OC3C24C1CCC(O3)(OO4)C)O)C
• Isomeric SMILES: C[C@@H]1CC[C@H]2[C@H](C(O[C@H]3[C@@]24[C@H]1CCC(O3)(OO4)C)O)C
• Uses: The main metabolite of Artemisinin, Arteether, Artemether, Artesunate. An active antimalarial metabolite

Technology Process of (4S,5R,8S,9R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-ol

There total 9 articles about (4S,5R,8S,9R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

C12H13O2(CH3)3(O)(OO) (63968-64-9) → dihydroartemisinin (71939-50-9)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 1.25h;

DOI:10.1021/jm9603577

Reference yield: 98.0%

C12H13O2(CH3)3(O)(OO) (63968-64-9) → dihydroartemisinin (71939-50-9)

Guidance literature:

With methanol; sodium tetrahydroborate; at 0 ℃; for 3h;

DOI:10.1021/acsmedchemlett.9b00669

Reference yield: 85.0%

artemisinin (63968-64-9,113472-97-2,119241-68-8) → dihydroartemisinin (71939-50-9,81496-81-3,98672-75-4,122442-32-4,123930-80-3,131175-87-6)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 - 5 ℃; for 3h;

upstream raw materials:

C₁₂H₁₃O₂(CH₃)3(O)(OO)

artemotil

10α-(4-benzylpiperazin-1-yl)-10-deoxoartemisinin

dihydroartemisinic acid

Downstream raw materials:

9,10-dehydrodihydroartemisinin

artemether

C₂₀H₃₂O₇

10α-phenylthiodihydroartemisinin

Refernces

• 1、 Fan, Xiaolei,Sans, Victor,Yaseneva, Polina,Plaza, Dorota D.,Williams, Jonathan,Lapkin, Alexei. "Facile stoichiometric reductions in flow: An example of artemisinin". . p. 1039 - 1042. Retrieved 2012.
• 2、 Brossi,Venugopalan,Gerpe,Yeh,Flippen-Anderson,Buchs,Luo,Milhous,Peters. "Arteether, a new antimalarial drug: Synthesis and antimalarial properties". . p. 645 - 650. Retrieved 1988.
• 3、 Wu, Guolin,Cheng, Bao,Qian, Hui,Ma, Shengming,Chen, Qin. "Identification of HSP90 as a direct target of artemisinin for its anti-inflammatory activity: Via quantitative chemical proteomics". . p. 6854 - 6859. Retrieved 2019.
• 4、 Nyein, Chan Myae,Zhong, Xiaolin,Lu, Junfeng,Luo, Huijuan,Wang, Jiamin,Rapposelli, Simona,Li, Mingtao,Ou-Yang, Ying,Pi, Rongbiao,He, Xixin. "Synthesis and anti-glioblastoma effects of artemisinin-isothiocyanate derivatives". . p. 40974 - 40983. Retrieved 2018.
• 5、 Gotsbacher, Michael P.,Cho, Sung Min,Kim, Nam Hee,Liu, Fei,Kwon, Ho Jeong,Karuso, Peter. "Reverse Chemical Proteomics Identifies an Unanticipated Human Target of the Antimalarial Artesunate". . p. 636 - 643. Retrieved 2019.
• 6、 Teja-Isavadharm, Paktiya,Siriyanonda, Duangsuda,Siripokasupkul, Raveewan,Apinan, Roongnapa,Chanarat, Nitima,Lim, Apassorn,Wannaying, Srisombat,Saunders, David,Fukuda, Mark M.,Miller, Robert S.,Weina, Peter J.,Melendez, Victor. "A simplified liquid chromatography-mass spectrometry assay for artesunate and dihydroartemisinin, its metabolite, in human plasma". . p. 8747 - 8768. Retrieved 2010.
• 7、 Gaur, Rashmi,Cheema, Harveer Singh,Kumar, Yogesh,Singh, Suriya Pratap,Yadav, Dharmendra K.,Darokar, Mahendra Padurang,Khan, Feroz,Bhakuni, Rajendra Singh. "In vitro antimalarial activity and molecular modeling studies of novel artemisinin derivatives". . p. 47959 - 47974. Retrieved 2015.
• 8、 Chen, Xuemei,Huang, Pei,Wang, Jing,Tian, Runmei,Chen, Yan,Chen, Yongzheng,Zhang, Lei,Ma, Zhigui. "Identification of H2S/NO-donating artemisinin derivatives as potential antileukemic agents". . p. 501 - 511. Retrieved 2019.
• 9、 Jaziri, Mondher,Diallo, Billo,Vanhaelen, Maurice,Homes, Jacques,Yoshimatsu, Kayo,Shimomura, Koichiro. "IMMUNODETECTION OF ARTEMISININ IN ARTEMISIA ANNUA CULTIVATED IN HYDROPONIC CONDITIONS". . p. 821 - 826. Retrieved 1993.
• 10、 Ferreira, Jorge F.S.,Janick, Jules. "Immunoquantitative analysis of artemisinin from Artemisia annua using polyclonal antibodies". . p. 97 - 104. Retrieved 1996.