10309-44-1

Basic information

• Product Name: 1-((E)-(S)-3,7-DIMETHYL-3-VINYL-OCTA-1,6-DIENYL)-4-METHOXY-BENZENE
• Synonyms: 1-((E)-(S)-3,7-DIMETHYL-3-VINYL-OCTA-1,6-DIENYL)-4-METHOXY-BENZENE;1-[(1E,3S)-3-Vinyl-3,7-dimethyl-1,6-octadienyl]-4-methoxybenzene;O-Methylbakuchiol
• CAS NO: 10309-44-1
• Molecular Formula: C₁₉H₂₆O
• Molecular Weight: 270.40914
• Mol File: 10309-44-1.mol
• Article Data: 18

Chemical Properties

• Appearance: /
• Refractive Index: 1.53
• CAS DataBase Reference: 1-((E)-(S)-3,7-DIMETHYL-3-VINYL-OCTA-1,6-DIENYL)-4-METHOXY-BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-((E)-(S)-3,7-DIMETHYL-3-VINYL-OCTA-1,6-DIENYL)-4-METHOXY-BENZENE(10309-44-1)
• EPA Substance Registry System: 1-((E)-(S)-3,7-DIMETHYL-3-VINYL-OCTA-1,6-DIENYL)-4-METHOXY-BENZENE(10309-44-1)

Safety Data

• Hazardous Substances Data: 10309-44-1(Hazardous Substances Data)

Usage

Description

1-((E)-(S)-3,7-DIMETHYL-3-VINYL-OCTA-1,6-DIENYL)-4-METHOXY-BENZENE is a chemical compound characterized by a benzene ring with a methoxy group and an eight-carbon hydrocarbon chain featuring a double bond, two methyl groups, and one vinyl group. 1-((E)-(S)-3,7-DIMETHYL-3-VINYL-OCTA-1,6-DIENYL)-4-METHOXY-BENZENE, a derivative of 4-methoxybenzene or anisole, is known for its unique structure and reactivity, making it a versatile intermediate in organic chemistry.

Uses

Used in Fragrance Industry:
1-((E)-(S)-3,7-DIMETHYL-3-VINYL-OCTA-1,6-DIENYL)-4-METHOXY-BENZENE is used as a key intermediate for the synthesis of various fragrances due to its aromatic properties and the presence of a long hydrocarbon chain with a double bond.
Used in Flavoring Industry:
In the flavoring industry, 1-((E)-(S)-3,7-DIMETHYL-3-VINYL-OCTA-1,6-DIENYL)-4-METHOXY-BENZENE is utilized as a building block for creating diverse flavor compounds, capitalizing on its unique chemical structure and reactivity.
Used in Pharmaceutical Industry:
1-((E)-(S)-3,7-DIMETHYL-3-VINYL-OCTA-1,6-DIENYL)-4-METHOXY-BENZENE serves as an important intermediate in the development of pharmaceuticals, benefiting from its potential for diversification and the presence of functional groups that can be further modified for specific medicinal applications.
Used in Organic Chemistry:
As a valuable intermediate in organic chemistry, 1-((E)-(S)-3,7-DIMETHYL-3-VINYL-OCTA-1,6-DIENYL)-4-METHOXY-BENZENE is used for the synthesis of a wide range of organic compounds, taking advantage of its reactive double bond and the versatility of its hydrocarbon chain.

InChI:InChI=1/C19H26O/c1-6-19(4,14-7-8-16(2)3)15-13-17-9-11-18(20-5)12-10-17/h6,8-13,15H,1,7,14H2,2-5H3/b15-13+/t19-/m1/s1

Upstream product

• 60657-35-4 (Z)-6-(4-Methoxy-phenyl)-4-methyl-4-vinyl-hex-5-enal 
• 24470-78-8 isopropyltriphenylphosphonium iodide 
• 60657-33-2 C₂₁H₃₀O₃ 
• 60657-34-3 (Z)-6-(4-Methoxy-phenyl)-4-methyl-4-vinyl-hex-5-en-1-ol 
• 214907-25-2 (4-methoxystyrene)boronic acid 
• 91940-11-3 (3,7-dimethylocta-1,6-diene-3-sulfonyl)benzene 
• 17015-60-0 bakuchiol 
• 74-88-4 methyl iodide 
• 1217536-40-7 (R)-1-(4-Methoxy-phenyl)-3,7-dimethyl-3-vinyl-octane-1,7-diol 
• 1020108-56-8 (3S)-3-ethenyl-1-(4-methoxyphenyl)-3,7-dimethyloct-6-en-2-yl methanesulfonate 
• 1530-33-2 isopropyltriphenylphosphonium bromide 
• 60699-32-3 (E)-3,7-dimethylocta-2,6-dien-1-yl diethyl phosphate 
• 768-60-5 4-methoxyphenylacetylen 
• 1201917-34-1 (R)-(-)-3-vinyl-3,7-dimethyloct-6-enal 

Downstream Products

• 43010-55-5 Hexahydrobakuchiol-methylether 
• 17015-60-0 bakuchiol 
• 54154-45-9 1-methoxy-4-((1S,2S,5R)-5-methyl-2-(prop-1-en-2-yl)-5-vinylcyclohexyl)benzene 
• 54154-44-8 1-methoxy-4-((1R,2R,5R)-5-methyl-2-(prop-1-en-2-yl)-5-vinylcyclohexyl)benzene 
• 74921-97-4 2-hydroxybakuchiol methyl ether 
• 54154-50-6 1-((R)-2-Isopropyl-5-methyl-5-vinyl-cyclohex-1-enyl)-4-methoxy-benzene 
• 54274-55-4 1-((1S,2R)-2-Isopropyl-5,5-dimethyl-cyclohexyl)-4-methoxy-benzene 
• 54154-49-3 1-((1R,2S)-2-Isopropyl-5,5-dimethyl-cyclohexyl)-4-methoxy-benzene 
• 54154-48-2 1-((1S,2R,5R)-2-Isopropyl-5-methyl-5-vinyl-cyclohexyl)-4-methoxy-benzene 
• 54154-47-1 1-((1R,2S,5R)-2-Isopropyl-5-methyl-5-vinyl-cyclohexyl)-4-methoxy-benzene 
• 43010-57-7 2,3,16,17-Tetrahydrobakuchiol-methylether 
• 43010-56-6 8-Acetoxy-hexahydrobakuchiol-methylether 
• 1020108-62-6 4-[(1E,3R)-3-ethenyl-3,7-dimethylocta-1,6-dienyl]phenol 
• 1361320-50-4 (S)-4-{3-(4-methoxystyryl)-3,7-dimethylocta-1,6-dienyl}phenol 

Relevant articles and documents

Combining Palladium and Chiral Organocatalysis for the Enantioselective Deconjugative Allylation of Enals via Dienamine Intermediates

A catalytic enantioselective deconjugative allylation of enals is reported. A variety of enals underwent this transformation in high yield and ee, and products can be readily transformed into γ-allyl enals via a Cope rearrangement without erosion of ee. This transformation was used to install the quaternary stereocenter in (S)-bakuchiol, enabling completion of a concise formal synthesis.

Synthesis of Chiral Tertiary Boronic Esters: Phosphonate-Directed Catalytic Asymmetric Hydroboration of Trisubstituted Alkenes

Highly enantioselective rhodium-catalyzed hydroboration of allylic phosphonates by pinacolborane affords chiral tertiary boronic esters. The β-borylated phosphonates are readily converted to chiral β- and γ-hydroxyphosphonates and aminophosphonates and to phosphonates bearing a quaternary carbon stereocenter. The utility of the latter is illustrated by the synthesis of (S)-(+)-bakuchiol methyl ether.

Anti-proliferative evaluation of monoterpene derivatives against leukemia

The cure rate of pediatric acute lymphoblastic leukemia (ALL) has significantly improved in the past thirty years, however not all patient cohorts respond well to current chemotherapy regimens. Among the high risk patient cohort is infants with MLL-rearranged (MLL-r) B-ALL, which remains dismal with an overall survival rate 35%. Our program is interested in identifying new molecular scaffolds to better understand the underlying mechanisms and ultimately provide new targeted treatments. Based on a phenotypic screen, phenolic natural products were identified as promising scaffolds for further chemical evaluation. Herein we disclose the effects of a potent anti-proliferative compound 31 against human ALL leukemia cellular models.