114311-70-5

Basic information

• Product Name: 1-HYDROXY-6,6-DIMETHYL-2-HEPTENE-4-YNE
• Synonyms: 2-HEPTEN-4-YN-1-OL, 6,6-DIMETHYL-;1-HYDROXY-6,6-DIMETHYL-2-HEPTENE-4-YNE;1-Hydroxy-6,6-dimetnyl-2-heptene-4-yne;6,6-DiMethyl-2-hepten-4-yne-1-ol
• CAS NO: 114311-70-5
• Molecular Formula: C9H14O
• Molecular Weight: 138.21
• Mol File: 114311-70-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 229.089 °C at 760 mmHg
• Flash Point: 99.126 °C
• Appearance: /
• Density: 0.912 g/cm³
• Refractive Index: 1.483
• CAS DataBase Reference: 1-HYDROXY-6,6-DIMETHYL-2-HEPTENE-4-YNE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-HYDROXY-6,6-DIMETHYL-2-HEPTENE-4-YNE(114311-70-5)
• EPA Substance Registry System: 1-HYDROXY-6,6-DIMETHYL-2-HEPTENE-4-YNE(114311-70-5)

Safety Data

• Hazardous Substances Data: 114311-70-5(Hazardous Substances Data)

Usage

General Description

1-Hydroxy-6,6-dimethyl-2-heptene-4-yne, also known as trogerol, is a synthetic chemical compound used in the production of various personal care products and cosmetics. It is a clear, colorless liquid with a faint odor and is commonly used as a fragrance ingredient and emollient in skincare and hair care products. Trogerol is known for its moisturizing properties and ability to soften and smooth the skin. It is often used in anti-aging and moisturizing creams, lotions, and serums. Additionally, this compound has potential use in pharmaceuticals and as a food additive, although further research is needed to fully understand its potential applications in these areas. Trogerol is considered to be safe when used in accordance with regulations and guidelines set forth by relevant authorities.

InChI:InChI=1/C9H14O/c1-9(2,3)7-5-4-6-8-10/h4,6,10H,8H2,1-3H3

Upstream product

• 54599-49-4 ethyl 6,6-dimethyl-2-hepten-4-ynoate 
• 126764-15-6 (E/Z)-1-bromo-6,6-dimethylhept-2-ene-4-yne 
• 52323-98-5 4,4-dimethylpent-2-yn-1-ol 
• 78629-21-7 (E)-6,6-dimethyl-2-hepten-4-ynyl bromide 

Downstream Products

• 91161-71-6 terbinafin 

Relevant articles and documents

Identification of a reactive metabolite of terbinafine: Insights into terbinafine-induced hepatotoxicity

Oral terbinafine treatment for superficial fungal infections of toe and fingernails is associated with a low incidence (1:45000) of hepatobiliary dysfunction. Due to the rare and unpredictable nature of this adverse drug reaction, the mechanism of toxicity has been hypothesized to be either an uncommon immunological or metabolically mediated effect. However, there is little evidence to support either mechanism, and toxic metabolites of terbinafine have not been identified. We incubated terbinafine with both rat and human liver microsomal protein in the presence of GSH and were able to trap an allylic aldehyde, 7,7-dimethylhept-2-ene-4-ynal (TBF-A), which corresponds to the N-dealkylation product of terbinafine. TBF-A was also prepared synthetically and reacted with excess GSH to yield conjugates with HPLC retention times and mass spectra identical to those generated in the microsomal incubations. The major GSH conjugate, characterized by 1H NMR, corresponds to addition of GSH in a 1,6-Michael fashion. There remains a second electrophilic site on this metabolite, which can bind either to a second molecule of GSH or to cellular proteins via a 1,4-Michael addition mechanism. Moreover, we demonstrated that the formation of the GSH conjugates was reversible. We speculate that this allylic aldehyde metabolite, formed by liver enzymes and conjugated with GSH, would be transported across the canalicular membrane of hepatocytes and concentrated in the bile. The mono-GSH conjugate, which is still reactive, could bind to hepatobiliary proteins and lead to direct toxicity. Alternatively, it could modify canalicular proteins and lead to an immune-mediated reaction causing cholestatic dysfunction.

Synthesis of vinylallenes by conjugate 1,6-, 1,8-, 1,10- and 1,12-addition reactions of organocuprates with acetylenic Michael acceptors and their use as dienes in intermolecular Diels-Alder reactions

Various vinylallenes were synthesized by conjugate cuprate additions to acetylenic Michael acceptors. Thus, 1,6-addition reactions with 2-en-4-ynoates 1, 3, and 5a, respectively, furnished vinylallenes 2, 4, and 7 after regioselective electrophilic capture of the allenyl enolates formed. Likewise, 1,8-addition to 2,4-dien-6-ynoates 8a and 10 gave the vinylallenes 9 and 11, whereas the 1,10-addition of Me2CuLi to 2,4,6-trien-8-ynoate 12 provided allene 13, and the analogous 1,12-addition to 2,4,6,8-tetraen-10-ynoate 14 furnished the polyene 15. These vinylallenes are valuable dienophiles in regio- and stereoselective Diels-Alder reactions, as evidenced by the formation of the cycloaddition products 16-24. In the presence of Lewis acids, vinylallene 4a presumably rearranges to a cyclopentadiene derivative which then forms the cycloadducts 25 and 26. VCH Verlagsgesellschaft mbH, 1996.