Lathyrol

Base Information

• Chemical Name: Lathyrol
• CAS No.: 34420-19-4
• Molecular Formula: C20H30O4
• Molecular Weight: 334.456
• ChEMBL ID: CHEMBL3426445
• DSSTox Substance ID: DTXSID301099102
• Metabolomics Workbench ID: 70217
• Mol file: 34420-19-4.mol

Synonyms:Lathyrol;34420-19-4;(1aR,2E,4aR,6S,7S,7aR,8R,11aS)-1,1a,4a,5,6,7,7a,8,9,10,11,11a-Dodecahydro-4a,7,8-trihydroxy-1,1,3,6-tetramethyl-9-methylene-4H-cyclopenta[a]cyclopropa[f]cycloundecen-4-one;CHEMBL3426445;SCHEMBL11126028;DTXSID301099102;HY-N0561;s3921;AKOS030629538;CS-6026;AC-33972;NS00093863

Chemical Property of Lathyrol

Chemical Property:

• Vapor Pressure: 3.01E-12mmHg at 25°C
• Refractive Index: 1.566
• Boiling Point: 503.537 °C at 760 mmHg
• PKA: 12.17±0.70(Predicted)
• Flash Point: 272.422 °C
• PSA: 77.76000
• Density: 1.182 g/cm³
• LogP: 2.23290
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 334.21440943
• Heavy Atom Count: 24
• Complexity: 605

Purity/Quality:

Lathyrol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2(C(C1O)C(C(=C)CCC3C(C3(C)C)C=C(C2=O)C)O)O
• Isomeric SMILES: C[C@H]1C[C@]2([C@H]([C@H]1O)[C@H](C(=C)CC[C@H]3[C@H](C3(C)C)/C=C(/C2=O)\C)O)O
• Uses: Lathyrol is a chemical constituent found in the seeds of Euphorbia lathyris that could induce leukemia in SWR mice.

Technology Process of Lathyrol

There total 6 articles about Lathyrol 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: 89.0%

(12E,2S,3S,4R,5R,9S,11R,15R)-5,15-diacetoxy-3-benzoyloxylathyra-6(17),12-dien-14-one → (4aR,6S,7S,7aR,8R,E)-4a,7,8-trihydroxy-1,1,3,6-tetramethyl-9-methylene-4a,5,6,7,7a,8,9,10,11,11a-decahydro-1H-cyclopenta[a]cyclopropa[f][11]annulen-4(1aH)-one (34420-19-4)

Guidance literature:

With potassium hydroxide; In methanol; at 20 ℃; for 24h;

DOI:10.1021/acs.jmedchem.5b00058

Reference yield: 80.0%

3,5,15-tri-O-acetyllathyrol (1613699-95-8) → (4aR,6S,7S,7aR,8R,E)-4a,7,8-trihydroxy-1,1,3,6-tetramethyl-9-methylene-4a,5,6,7,7a,8,9,10,11,11a-decahydro-1H-cyclopenta[a]cyclopropa[f][11]annulen-4(1aH)-one (34420-19-4)

Guidance literature:

With potassium hydroxide; In methanol; at 20 ℃; for 24h;

DOI:10.1016/j.bmc.2017.04.016

Reference yield: 78.0%

5α,15β‐diacetoxy‐3β‐propanoyloxy‐lathyr‐6(17),12E‐en‐14‐one → (4aR,6S,7S,7aR,8R,E)-4a,7,8-trihydroxy-1,1,3,6-tetramethyl-9-methylene-4a,5,6,7,7a,8,9,10,11,11a-decahydro-1H-cyclopenta[a]cyclopropa[f][11]annulen-4(1aH)-one (34420-19-4)

Guidance literature:

With potassium hydroxide; In methanol; at 20 ℃; for 3h;

DOI:10.1002/pca.2841

upstream raw materials:

lathyrol-3-phenylacetate-5,15-diacetate

3,5,15-tri-O-acetyllathyrol

Refernces

• 1、 Jiao, Wei,Wan, Zhongmin,Chen, Shuang,Lu, Runhua,Chen, Xiaozhen,Fang, Dongmei,Wang, Jiufeng,Pu, Shengcai,Huang, Xin,Gao, Haixiang,Shao, Huawu. "Lathyrol diterpenes as modulators of P-glycoprotein dependent multidrug resistance: Structure-activity relationship studies on Euphorbia factor L3 derivatives". . p. 3720 - 3738. Retrieved 2015.
• 2、 Neto, Sara,Duarte, Noélia,Pedro, Cecília,Spengler, Gabriella,Molnár, Joséph,Ferreira, Maria-José U.. "Effective MDR reversers through phytochemical study of Euphorbia boetica". . p. 498 - 511. Retrieved 2019.
• 3、 Wang, Wang,Xiong, Liangliang,Li, Yutong,Song, Zhuorui,Sun, Dejuan,Li, Hua,Chen, Lixia. "Synthesis of lathyrane diterpenoid nitrogen-containing heterocyclic derivatives and evaluation of their anti-inflammatory activities". . . Retrieved 2022/01/24.