62299-38-1

Upstream product

• 6138-90-5 trans-geranyl bromide 
• 123-08-0 4-hydroxy-benzaldehyde 
• 106-24-1 Geraniol 

Downstream Products

• 92832-23-0 (Z)-2-Azido-3-[4-((E)-3,7-dimethyl-octa-2,6-dienyloxy)-phenyl]-acrylic acid ethyl ester 
• 6901-87-7 (6S,3Z)-3-(4-(3,7-dimethylocta-2,6-dienyloxy)benzylidene)-6-methylpiperazine-2,5-dione 
• 6901-87-7 deoxymicelianamide 
• 225650-11-3 4'-geranyloxy-5,7-dimethoxymethoxyflavanone 
• 225650-12-4 4-geranyloxy-2-hydroxyl-4',6'-dimethoxymethoxychalcone 

Relevant academic research and scientific papers

Total Synthesis of (+/-)-Mycelianamide

The first total synthesis of the antibiotic (+/-)-mycelianamide has been achieved using p-geranyloxybenzaldehyde and ethyl nitroacetate as starting materials.

An intramolecular Heck reaction that prefers a 5-endo- to a 6-exo-trig cyclization pathway

A regioselective aromatic Claisen rearrangement was used to prepare 17a, the precursor of triflate 17e. The intramolecular Heck reaction of 17e is promoted only by bidentate phosphine ligands, giving exclusively and in excellent yield 20, the product of a 5-endo-trig cyclization, despite the possibility for a 6-exo-trig pathway. Georg Thieme Verlag Stuttgart.

BIOSYNTHESIS OF CHEMICALLY DIVERSIFIED NON-NATURAL TERPENE PRODUCTS

The disclosure relates to compounds of the formulae (l)-(IV) and their use as substrates for making terpenoids. New substrates for terpene biosynthesis and methods for making new types of terpenes are described herein. Diterpenes occupy a unique molecular

Natural and semisynthetic oxyprenylated aromatic compounds as stimulators or inhibitors of melanogenesis

It has been very recently shown how naturally occurring oxyprenylated coumarins are effective modulators of melanogenesis. In this short communication we wish to generalize the potentialities as skin tanning or whitening agents of a wider panel of natural and semisynthetic aromatic compounds, including coumarins, cinnamic and benzoic acids, cinnamaldehydes, benzaldehyde, and anthraquinone derivatives. A total number of 43 compounds have been tested assaying their capacity to inhibit or stimulate melanin biosynthesis in cultured murine Melan A cells. The wider number of chemicals herein under investigation allowed to depict a detailed structure-activity relationship, as the following: (a) benzoic acid derivatives are slightly pigmenting agent, for which the effect is more pronounced in compounds with longer O-side chains; (b) independently from the type of substitution, cinnamic acids are able to increase melanin biosynthesis, while benzaldehydes are able to decrease it; (c) coumarins with a 3,3-dimethylallyl or shorter skeletons as substituents in position 7 are tanning agents, while coumarins with farnesyloxy groups are whitening ones; (d) double oxyprenylation in position 6 and 7 and 3,3-dimethylallyl or geranyl skeletons have slight depigmenting capacities, while farnesyl skeletons tend to marginally increase the tanning effect; (e) the presence of electron withdrawing groups (acetyl, COOH, and -Cl) and geranyl or farnesyl oxyprenylated chains respectively in positions 3 and 7 of the coumarin nucleus lead to a whitening effect, and finally (f) oxyprenylated anthraquinones have only a weak depigmenting capacity.

A method of synthesis of [...] with oxygen (by machine translation)

The invention discloses a method for synthesizing [...] oxygen substituted, to simple and cheap substituted acetophenone and substituted benzaldehyde as raw material through the six steps of the reaction to about 30% of the total yield of synthesis of nat

Synthesis method of oxygen substituting geranyl chalcone

The invention discloses a synthesis method of oxygen substituting geranyl chalcone. The lower-cost substituted hydroxyacetophenone and substituted hydroxybenzaldehyde are used as raw materials for synthesizing the natural products of chalcone with the hig

Synthesis and bioactivity of diketopiperazine PJ147 and its derivatives from Gliocladium sp. YUP08

Concise total synthesis of diketopiperazine PJ147, obtained from mycelium of Gliocladium sp. YUP08, has been achieved in seven steps with 43.5% overall yield. Biological evaluation of PJ147 exhibited strong inhibiting activity against A375-S2, Hela, P388, A-549, HL-60, and BEL-7420 cell lines. Thus, eight derivatives of PJ147 with high water solubility were also synthesized to facilitate the in vivo bioassay of this kind of diketopiperazines. 2014

Synthesis and anti-cancer activity of naturally occurring 2,5-diketopiperazines

Three naturally occurring oxyprenylated diketopiperazines were synthesized and preliminarily tested as growth inhibitory agents in vitro against various cancer cell lines. The compounds were tested on six human cancer cell lines with different sensitivity to proapoptotic stimuli using the MTT colorimetric assay. The data revealed that of the chemicals under study only deoxymicelianamide (11) displayed the highest activity, recording mean IC50 growth inhibitory values ranging from 2 to 23 μM. A comparative study with the non-geranylated saturated derivative of (11) revealed the importance of the presence of the geranyloxy side chain and the exocyclic 2,5-DPK double bond moiety for the observed activity.

Farnesyl diphosphate analogues with Aryl moieties are efficient alternate substrates for protein farnesyltransferase

Farnesylation is an important post-translational modification essential for the proper localization and function of many proteins. Transfer of the farnesyl group from farnesyl diphosphate (FPP) to proteins is catalyzed by protein farnesyltransferase (FTas

First total syntheses of 4'-O-geranylisoliquiritigenin and 4'-O geranylnarigenin

The title compounds , 4'-O-geranylisoliquiritigenin and 4'-O- geranylnaringenin isolated from Millettia ferruginea and Borania coerulescens respectively, were first synthesized starting from geranyl bromide , 4- hydroxybenzaldehyde and O-hydroxy acetophen