53915-41-6

Basic information

• Product Name: (-)-Nephthenol
• Synonyms: (-)-Nephthenol;(R,3E,7E,11E)-α,α,4,8,12-Pentamethylcyclotetradeca-3,7,11-triene-1-methanol;2-[(1R,4E,8E,12E)-4,8,12-Trimethyl-4,8,12-cyclotetradecatriene-1-yl]-2-propanol;Nephthenol;(R)-nephthenol
• CAS NO: 53915-41-6
• Molecular Formula: C₂₀H₃₄O
• Molecular Weight: 290.48
• Mol File: 53915-41-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 394.6°C at 760 mmHg
• Flash Point: 129.7°C
• Appearance: /
• Density: 0.881g/cm³
• Vapor Pressure: 7.32E-08mmHg at 25°C
• Refractive Index: 1.474
• CAS DataBase Reference: (-)-Nephthenol(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Nephthenol(53915-41-6)
• EPA Substance Registry System: (-)-Nephthenol(53915-41-6)

Safety Data

• Hazardous Substances Data: 53915-41-6(Hazardous Substances Data)

Usage

Description

(-)-Nephthenol, a cembrane diterpenoid, is a naturally occurring compound derived from the hydration of the exocyclic double bond of cembrene C. It exhibits unique chemical properties and potential biological activities, making it a valuable substance for various applications.

Uses

Used in Pharmaceutical Industry:
(-)-Nephthenol is used as a pharmaceutical compound for its potential therapeutic effects. Its unique chemical structure allows it to interact with specific biological targets, making it a promising candidate for the development of new drugs.
Used in Chemical Research:
(-)-Nephthenol serves as a valuable research tool in the field of organic chemistry. Its unique cembrane diterpenoid structure provides insights into the synthesis and properties of related natural products, contributing to the advancement of chemical knowledge.
Used in Cosmetic Industry:
(-)-Nephthenol may be used as an active ingredient in the cosmetic industry due to its potential beneficial effects on skin health. Its incorporation into skincare products could provide users with improved skin quality and appearance.
Used in Agricultural Industry:
(-)-Nephthenol could potentially be utilized in the agricultural industry as a natural pesticide or growth regulator. Its unique chemical properties may offer new approaches to pest control and crop management, promoting sustainable agricultural practices.

InChI:InChI=1/C20H34O/c1-16-8-6-10-17(2)12-14-19(20(4,5)21)15-13-18(3)11-7-9-16/h8,11-12,19,21H,6-7,9-10,13-15H2,1-5H3/b16-8+,17-12+,18-11+/t19-/m0/s1

Upstream product

• 6699-20-3 (E,E,E)-geranylgeranyl diphosphate 
• 910247-30-2 (R,3E,7E,11E)-benzyl 4,8,12-trimethylcyclotetradeca-3,7,11-trienecarboxylate 
• 75-16-1 methylmagnesium bromide 
• 132274-03-4 (2R,3R,all-E)-2,3-Epoxy-2,6,10,14-tetramethyl-16-(phenylthio)hexadeca-6,10,14-trien-1-ol 
• 132274-04-5 Toluene-4-sulfonic acid (2R,3R)-2-methyl-3-((3E,7E,11E)-3,7,11-trimethyl-13-phenylsulfanyl-trideca-3,7,11-trienyl)-oxiranylmethyl ester 
• 132274-01-2 <(all-E)-2,6,10,14-Tetramethyl-16-(phenylthio)hexadeca-2,6,10,14-tetraen-1-yl>-acetat 
• 132274-05-6 (2S,3R)-2-Iodomethyl-2-methyl-3-((3E,7E,11E)-3,7,11-trimethyl-13-phenylsulfanyl-trideca-3,7,11-trienyl)-oxirane 
• 132274-02-3 (all-E)-2,6,10,14-Tetramethyl-16-(phenylthio)hexadeca-2,6,10,14-tetraen-1-ol 
• 132274-00-1 <(all-E)-14-Hydroxy-2,6,10,14-tetramethylhexadeca-2,6,10,15-tetraen-1-yl>-acetat 
• 132340-75-1 (all-E)-2,6,10,14-Tetramethylhexadeca-2,6,10,15-tetraen-1,14-diol 
• 132273-99-5 (all-E)-15-Hydroxy-6,10,14-trimethylpentadeca-5,9,13-trien-2-on 
• 1117-52-8 6,10,14-trimethyl-5,9,13-pentadecatriene-2-on 
• 63859-99-4 (14R,all-E)-14,15-Epoxy-3,7,11,15-tetramethyl-1-(phenylthio)hexadeca-2,6,10-trien 
• 110202-75-0 2-((3E,7E,11E)-(R)-4,8,12-Trimethyl-cyclotetradeca-3,7,11-trienyl)-propane-1,2-diol 

Downstream Products

• 38746-47-3 (R)-5,5-dimethyl-4-(3-oxo-butyl)-dihydro-furan-2-one 
• 38748-84-4 (–)-(R)-cembrene A 

Relevant articles and documents

Targeting active site residues and structural anchoring positions in terpene synthases

The sesterterpene synthase SmTS1 from Streptomyces mobaraensis contains several unusual residues in positions that are otherwise highly conserved. Site-directed mutagenesis experiments for these residues are reported that showed different effects, resulting in some cases in an improved catalytic activity, but in other cases in a loss of enzyme function. For other enzyme variants a functional switch was observed, turning SmTS1 from a sesterterpene into a diterpene synthase. This article gives rational explanations for these findings that may generally allow for protein engineering of other terpene synthases to improve their catalytic efficiency or to change their functions.

Novel Synthesis of (-)-(R)-Cembrene A, Synthesis of (+)-(R)-Cembrenene and (+)-(S)-Cembrene

A novel synthesis of (-)-(R)-cembrene A ((-)-3) was developed using the Sharpless epoxidation for the introduction of the chiral center.Furthermore, the synthesis of (+)-(R)-cembrenene ((+)-4) showed that this cembranoid must have the (R)-configuration and not, as previously reported, the (S)-confguration.Selective hydrogebation of (+)-4 afforded (+)-(S)-cembrene ((+)-5).

Marine Terpenes and Terpenoids. III. Isolation and Structures of Two Cembrane Diols from the Soft Coral Sinularia mayi

Nine cembrane-type diterpenes were isolated from the lipid extract of the soft coral, Sinularia mayi.Of these, seven α-methylene-γ-lactone derivatives (1-7) had been previously isolated from various soft corals.The structures of the two new cembrane diols, sinulariol A (8a) and sinulariol B (9), were determined by means of spectroscopic analyses, and compound 9 was chemically correlated with nephthenol (11) whose absolute configuration is known.Compounds 8a, and 9 are plausible precursors to the cembrane lactones found in various soft corals.Keywords-Coelenterata; alcyonarian; soft coral; Sinularia mayi; cembrane diol; sinulariol A; sinulariol B