4698-08-2

Basic information

• Product Name: 2,6-Octadienoic acid, 3,7-dimethyl-, (E)-
• Synonyms: 2,6-Octadienoic acid, 3,7-dimethyl-, (2E)-;2,6-Octadienoic acid, 3,7-dimethyl-, (E)-;(2E)-3,7-dimethylocta-2,6-dienoic acid;(3E)-3,7-Dimethyl-2,6-octadienoic acid;(E)-3,7-Dimethyl-2,6-octadienoic acid;Geranic acid a;trans-Geranic acid
• CAS NO: 4698-08-2
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.23
• Mol File: 4698-08-2.mol
• Article Data: 23

Chemical Properties

• Melting Point: 81 °C
• Boiling Point: 295.3°Cat760mmHg
• Flash Point: 201.1°C
• Appearance: /
• Density: 0.96g/cm³
• PKA: 5.17±0.33(Predicted)
• CAS DataBase Reference: 2,6-Octadienoic acid, 3,7-dimethyl-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Octadienoic acid, 3,7-dimethyl-, (E)-(4698-08-2)
• EPA Substance Registry System: 2,6-Octadienoic acid, 3,7-dimethyl-, (E)-(4698-08-2)

Safety Data

• Hazardous Substances Data: 4698-08-2(Hazardous Substances Data)

Usage

General Description

2,6-Octadienoic acid, 3,7-dimethyl-, (E)- is a chemical compound commonly known as geraniol, a natural flavor and fragrance compound found in a variety of plants. It has a sweet rose-like scent and is commonly used in the production of perfumes, soaps, and flavorings. Geraniol is also known for its potential health benefits, including its antimicrobial, antioxidant, and anti-inflammatory properties. It is used in traditional medicine to treat various ailments such as pain and inflammation, and it also shows promise in the field of cancer research due to its potential as an anti-tumor agent. Additionally, geraniol has been studied for its potential as an insect repellent and is commonly used in the manufacturing of mosquito repellents.

Upstream product

• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 106-26-3 cis-3,7-dimethyl-2,6-octadienal 
• 141-27-5 3,7-dimethyl-2,6-octadienal 
• 106-24-1 Geraniol 
• 32659-21-5 ethyl (E)-3,7-dimethylocta-2,6-dienoate 
• 37586-57-5 4-methyl-3-pentenylmagnesium bromide 
• 541-47-9 3-Methylbutenoic acid 
• 870-63-3 prenyl bromide 
• 125259-15-6 (E)-3,7-Dimethyl-octa-2,6-dienoic acid (E)-1-methyl-3-phenyl-allyl ester 
• 106262-58-2 (E)-3,7-Dimethyl-octa-2,6-dienoic acid 3-methyl-but-2-enyl ester 
• 55050-39-0 3-Methylene-7-methyloct-6-enoic Acid 
• 60156-17-4 3-Benzenesulfonyl-3,7-dimethyl-oct-6-enoic acid ethyl ester 

Downstream Products

• 1195-32-0 1-methyl-4-isopropenylbenzene 
• 16750-87-1 (+/-)-filifolon 
• 491-09-8 3-terpinolenone 
• 55298-92-5 methyl 3-methylene-7-methyl-6-octenoate 
• 1189-09-9 methyl geranate 
• 18951-85-4 (R)-citronellic acid 
• 2111-53-7 (S)-(-)-citronellic acid 
• 58558-13-7 (2E)-3,7-dimethyl-2,6-octadienoyl chloride 
• 24190-30-5 (S)-α-cyclogeraniumsaeure 
• 13066-51-8 γ-geraniol 
• 55298-95-8 (5,5-dimethyl-cyclohex-1-enyl)-acetic acid methyl ester 
• 55298-96-9 (3,3-Dimethyl-cyclohex-1-enyl)-acetic acid methyl ester 
• 26532-23-0 (Z)-3,3-Dimethylcyclohexane-Δ^1,β-ethanol 
• 30346-23-7 3,3-Dimethyl-Z-cyclohexylidenessigsaeuremethylester 

Relevant articles and documents

Amides as bioisosteres of triazole-based geranylgeranyl diphosphate synthase inhibitors

Geranylgeranyl diphosphate synthase (GGDPS) inhibitors are of potential therapeutic interest as a consequence of their activity against the bone marrow cancer multiple myeloma. A series of bisphosphonates linked to an isoprenoid tail through an amide linkage has been prepared and tested for the ability to inhibit GGDPS in enzyme and cell-based assays. The amides were designed as analogues to triazole-based GGDPS inhibitors. Several of the new compounds show GGDPS inhibitory activity in both enzyme and cell assays, with potency dependent on chain length and olefin stereochemistry.

Divergent synthesis of four isomers of 6,7-dihydroxy-3,7-dimethyloct-2-enoic acid, esters and evaluation for the antifungal activity

The four isomers of 6,7-dihydroxy-3,7-dimethyloct-2-enoic acid 2 were synthesized via the selective direct Sharpless asymmetry dihydroxylation of geraniol as the key step in 35.0%-48.0% overall yields with 91.9%-97.7% ee values for esters 4 and 31.3%-36.4% overall yields with 90.3-97.5% ee values for acids 2 using cis- and trans-geraniol as raw materials. Their structures were characterized by 1H, 13C NMR and HR-ESI-MS data. The in vivo bioassay results showed that the chiral acid (Z, S)-2 was a good lead compound with 80%-100% inhibitory rates against P. cubensis, E. graminis, P. sorghi and C. gloeosporioides at the concentration of 400μg/mL.