38011-83-5

Basic information

• Product Name: Benzene, 1-[(3E)-4,8-dimethyl-3,7-nonadienyl]-4-methoxy-
• Synonyms: (3E)-4,8-dimethyl-1-(4-methoxyphenyl)-3,7-nonadiene;(E)-4-homogeranylphenyl methyl ether;Benzene,1-[(3E)-4,8-dimethyl-3,7-nonadienyl]-4-methoxy;(6E)-9-p-Methoxyphenyl-2,6-dimethylnona-2,6-diene;(E)-4-homogeranylanisole;4-homogeranylanisole;Benzene,1-(4,8-dimethyl-3,7-nonadienyl)-4-methoxy
• CAS NO: 38011-83-5
• Molecular Formula: C18H26O
• Molecular Weight: 258.404
• Mol File: 38011-83-5.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: Benzene, 1-[(3E)-4,8-dimethyl-3,7-nonadienyl]-4-methoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-[(3E)-4,8-dimethyl-3,7-nonadienyl]-4-methoxy-(38011-83-5)
• EPA Substance Registry System: Benzene, 1-[(3E)-4,8-dimethyl-3,7-nonadienyl]-4-methoxy-(38011-83-5)

Safety Data

• Hazardous Substances Data: 38011-83-5(Hazardous Substances Data)

Upstream product

• 6138-90-5 trans-geranyl bromide 
• 38769-92-5 4-methoxybenzylmagnesium chloride 
• 106-24-1 Geraniol 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 824-94-2 p-methoxybenzyl chloride 
• 60699-32-3 (E)-3,7-dimethylocta-2,6-dien-1-yl diethyl phosphate 
• 623-12-1 4-chloromethoxybenzene 
• 425681-14-7 diethyl ((E)-4,8-dimethyl-3,7-nonadienyl)phosphonate 
• 5389-87-7 1-chloro-3,7-dimethylocta-2,6-diene 
• 35162-74-4 geranyl phenyl sulfide 

Downstream Products

• 10064-08-1 (+)-(5S,10S)-12-methoxypodocarpa-8,11,13-triene 
• 303962-71-2 (4aR,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-6-methoxy-1,1,4a-trimethylphenanthrene 
• 269719-13-3 3-(4-methoxyphenylethyl)-2,4,4-trimethyl-1-cyclohexene 
• 331233-75-1 (E)-4-(4,8-dimethylnona-3,7-dien-1-yl)phenol 
• 511-05-7 sugiol 
• 514-62-5 (+/-)-ferruginol 
• 106625-40-5 4-((E)-4,8-Dimethyl-nona-3,7-dienyl)-1,2-dimethoxy-benzene 
• 1252599-38-4 C₁₈H₂₆O₂ 
• 709667-29-8 C₁₈H₂₇BrO₂ 
• 83999-79-5 ((1S,2S,4aR,10aS)-2-Benzyloxy-6-methoxy-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-1-yl)-methanol 
• 83999-80-8 (E)-9-(4-Methoxy-phenyl)-2,6-dimethyl-nona-1,6-dien-3-ol 
• 425681-12-5 (E)-3-homogeranyl-4-(tert-butyldiphenylsilyloxy)benzene 

Relevant articles and documents

Scalable Total Synthesis of rac-Jungermannenones B and C

Reported is the first scalable synthesis of rac-jungermannenones B and C starting from the commercially available and inexpensive geraniol in 10 and 9 steps, respectively. The unique jungermannenone framework is rapidly assembled by an unprecedented regio

Design, synthesis and anthelmintic activity of 7-keto-sempervirol analogues

The plant-derived, diterpenoid 7-keto-sempervirol was recently reported to display moderate activity against larval stages of Schistosoma mansoni (IC50 = 19.1 μM) and Fasciola hepatica (IC50 = 17.7 μM), two related parasitic blood and liver flukes responsible for the neglected tropical diseases schistosomiasis and fascioliasis, respectively. Here, we aimed to increase the potency of 7-keto-sempervirol by total synthesis of 30 structural analogues. Subsequent screening of these new diterpenoids against juvenile and adult lifecycle stages of both parasites as well as the human HepG2 liver cell line and the bovine MDBK kidney cell line revealed structure-activity relationship trends. The most active analogue, 7d, displayed improved dual anthelmintic activity over 7-keto-sempervirol (IC50 ≈ 6 μM for larval blood flukes; IC50 ≈ 3 μM for juvenile liver flukes) and moderate selectivity (SI ≈ 4–5 for blood flukes, 8–13 for liver flukes compared to HepG2 and MDBK cells, respectively). Phenotypic studies using scanning electron microscopy revealed substantial tegumental alterations in both helminth species, supporting the hypothesis that the parasite surface is one of the main targets of this family of molecules. Further modifications of 7d could lead to greater potency and selectivity metrics resulting in a new class of broad-spectrum anthelmintic.

Practical and Efficient Strategy for Synthesis of Ferruginol, Sugiol, and Sugiol Methyl Ether from Geraniol

-