40716-66-3 Usage
Description
Nerolidol, also known as trans-Nerolidol, is a sesquiterpene found in various plants such as cabreuva oil, oil of neroli, balsam Peru, ylang ylang, and many others. It exhibits diverse biological activities, including antimicrobial, antioxidant, anticancer, and insecticidal properties.
Uses
Used in Antimicrobial Applications:
Nerolidol is used as an antimicrobial agent for inhibiting the growth of various bacteria and fungi, including S. aureus, B. subtilis, E. coli, and S. cerevisiae. It demonstrates effective inhibition with zones of inhibition measuring 10, 9, 10, and 4 mm, respectively.
Used in Antioxidant Applications:
Nerolidol is used as an antioxidant for reducing the production of reactive oxygen species (ROS), which can cause cellular damage and contribute to various diseases.
Used in Anticancer Applications:
Nerolidol is used as an anticancer agent for reducing the viability of CaCo-2 adenocarcinoma cells with an IC50 value of 28.7 mg/L. It may have potential applications in cancer treatment and prevention.
Used in Insecticidal Applications:
Nerolidol is used as an insecticide against A. aegypti larvae with a 24-hour LC50 value of 9 mg/L. It can be employed in pest control and vector-borne disease management.
Used in Fragrance Industry:
Nerolidol is used as a fragrance ingredient in the perfumery industry due to its pleasant and floral scent. It can be found in various essential oils and is used to enhance the aroma of perfumes, cosmetics, and other fragrance products.
Used in Pharmaceutical Industry:
Nerolidol has potential applications in the pharmaceutical industry as a result of its diverse biological activities. It can be used in the development of new drugs for various therapeutic areas, including antimicrobial, antioxidant, anticancer, and insecticidal treatments.
Preparation
By isolation from a suitable essential oil or by chemical synthesis.
Check Digit Verification of cas no
The CAS Registry Mumber 40716-66-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,0,7,1 and 6 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 40716-66:
(7*4)+(6*0)+(5*7)+(4*1)+(3*6)+(2*6)+(1*6)=103
103 % 10 = 3
So 40716-66-3 is a valid CAS Registry Number.
InChI:InChI=1/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3/b14-11+
40716-66-3Relevant articles and documents
Yasuda et al.
, p. 2621 (1976)
Stereochemical investigations on the biosynthesis of achiral (Z)-γ-bisabolene in Cryptosporangium arvum
Rinkel, Jan,Dickschat, Jeroen S.
supporting information, p. 789 - 794 (2019/04/17)
A newly identified bacterial (Z)-γ-bisabolene synthase was used for investigating the cyclisation mechanism of the sesquiterpene. Since the stereoinformation of both chiral putative intermediates, nerolidyl diphosphate (NPP) and the bisabolyl cation, is lost during formation of the achiral product, the intriguing question of their absolute configurations was addressed by incubating both enantiomers of NPP with the recombinant enzyme, which resolved in an exclusive cyclisation of (R)-NPP, while (S)-NPP that is non-natural to the (Z)-γ-bisabolene synthase was specifically converted into (E)-β-farnesene. A hypothetical enzyme mechanistic model that explains these observations is presented.
Prenyl Praxis: A Method for Direct Photocatalytic Defluoroprenylation
Priya, Sonal,Weaver, Jimmie D.
supporting information, p. 16020 - 16025 (2018/11/27)
The prenyl fragment is the quintessential constituent of terpenoid natural products, a diverse family which contains numerous members with diverse biological properties. In contrast, fluorinated and multifluorinated arenes make up an important class of anthropogenic molecules which are highly relevant to material, agricultural, and pharmaceutical industries. While allylation chemistry is well developed, effective prenylation strategies have been less forthcoming. Herein, we describe the photocatalytic defluoroprenylation, a powerful method that provides access to "hybrid molecules" that possess both the functionality of a prenyl group and fluorinated arenes. This approach involves direct prenyl group transfer under very mild conditions, displays excellent functional group tolerance, and includes relatively short reaction times (4 h), which is the fastest photocatalytic C-F functionalization developed to date. Additionally, the strategy can be extended to include allyl and geranyl (10 carbon fragment) transfers. Another prominent finding is a reagent-dependent switch in regioselectivity of the major product from para to ortho C-F functionalization.
