59376-58-8

Basic information

• Product Name: 2,4-UNDECADIEN-1-OL
• Synonyms: 2,4-UNDECADEN-1-OL;2,4-UNDECADIEN-1-OL;2,4-Undecaden-1-ol (mixture of stereoisomers);Undecadenol;undeca-2,4-dienol;2,4-UNDECADIEN-1-OL (MIXTURE OF STEREOISOMERS);(2Z,4Z)-UNDECA-2,4-DIEN-1-OL;Ai3-34390
• CAS NO: 59376-58-8
• Molecular Formula: C₁₁H₂₀O
• Molecular Weight: 168.28
• EINECS: 261-722-1
• Mol File: 59376-58-8.mol

Chemical Properties

• Boiling Point: 256.7°C at 760 mmHg
• Flash Point: 98.5°C
• Appearance: /
• Density: 0.88
• Vapor Pressure: 0.00227mmHg at 25°C
• Refractive Index: 1.4860 to 1.4890
• CAS DataBase Reference: 2,4-UNDECADIEN-1-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-UNDECADIEN-1-OL(59376-58-8)
• EPA Substance Registry System: 2,4-UNDECADIEN-1-OL(59376-58-8)

Safety Data

• Hazardous Substances Data: 59376-58-8(Hazardous Substances Data)

Usage

Uses

Used in Flavoring Industry:
2,4-Undecadien-1-ol is used as a flavoring agent for its distinctive strong fruity and citrus-like aroma, enhancing the taste and scent of various food products.
Used in Perfuming Industry:
2,4-Undecadien-1-ol is used as a fragrance ingredient in the perfume industry, contributing to the creation of complex and appealing scents in perfumes and other scented products.
Used in Food and Beverage Industry:
Although it is a manufactured substance, 2,4-Undecadien-1-ol is also used in the food and beverage industry to add a natural fruity and citrus-like flavor to certain products, as it can be found in some fruits.

InChI:InChI=1/C11H20O/c1-2-3-4-5-6-7-8-9-10-11-12/h7-10,12H,2-6,11H2,1H3/b8-7-,10-9-

Upstream product

• 629-05-0 n-octyne 
• 31508-11-9 undeca-1-en-4-yne 
• 82994-41-0 (E)-3-(tri-n-butylstannyl)-2-propen-1-ol 
• 52356-93-1 (Z)-1-octenyl iodide 
• 73303-09-0 lithium di(n-hexyl)cuprate 
• 107-19-7 propargyl alcohol 
• 107-18-6 allyl alcohol 
• 55976-14-2 (Z)-1,4-undecadiene 

Relevant articles and documents

Ligand effects on the stereochemistry of Stille couplings, as manifested in reactions of Z-alkenyl halides

Unexpected losses in stereochemistry from Stille reactions involving Z-alkenyl halides have been shown to be ligand dependent. A new set of reaction conditions has been developed that, in most cases, leads to highly stereoselective cross-couplings under mild conditions, along with improved yields.

Highly selective synthesis of conjugated dienoic and trienoic esters via alkyne elementometalation - Pd-catalyzed cross-coupling

All four stereoisomers (7-10) of ethyl undeca-2,4-dienoate were prepared in ≥98% isomeric purity by Pd-catalyzed alkenylation (Negishi coupling) using ethyl (E)- and (Z)-β-bromoacrylates. Although the stereoisomeric purity of the 2Z,4E-isomer (8) prepared by Suzuki coupling using conventional alkoxide and carbonate bases was ≤95%, as reported earlier, the use of CsF or nBu4NF as a promoter base has now been found to give all of 7-10 in ≥98% selectivity. Other widely known methods reveal considerable limitations. Heck alkenylation was satisfactory for the syntheses of the 2E,4E and 2E,4Z isomers of ≥98% purity, but the purity of the 2Z,4E isomer was ≤95%. Mutually complementary Horner-Wadsworth-Emmons and Still-Gennari (SG) olefinations are also of considerably limited scopes. Neither 2E,4Z nor 2Z,4Z isomer is readily prepared in ≥90% selectivity. In addition to (2Z,4E)-dienoic esters, some (2Z,4E,6E)- and (2Z,4E,6Z)-trienoic esters have been prepared in ≥98% selectivity by a newly devised Pd-catalyzed alkenylation-SG olefination tandem process. As models for conjugated higher oligoenoic esters, all eight stereoisomers for ethyl trideca-2,4,6-trienoate (23-30) have been prepared in ≥98% overall selectivity.

Palladium-catalysed Reaction of Vinylic Halides with Allylic Alcohols: A Highly Chemo-, Regio- and Stereo-controlled Synthesis of Conjugated Dienols

A new, direct, highly chemo-, regio- and stereo-controlled method for the construction of (E,E) and (E,Z) conjugated dienols from vinylic halides and allylic alcohols is described.

Structural Dynamics of Pentadienyl Metal-Compounds Bearing a Terminal Alkyl Substituent: Both 'Stereoselective' and 'Stereodefensive' Synthesis of a Natural Perfume

The (2Z,4E)-, (2E,4Z)- and (2E,4E)-isomers of 2,4-decandien-1-ol (5) have been obtained with high and predictable stereochemical homogeneity starting from both (Z)- and (E)-1,4-decadiene.These hydrocarbons were hydroxylated in a reaction sequence consisting of metallation (by means of s-butyllithium or butyllithium/potassium-t-butoxide, giving rise to organometallic intermediates of specific conformations), dimethoxyborylation and oxidation.The different decadienols as well as (2E,4Z)-2,4-undecadien-1-ol were converted into the isovalerates, the ester derived from (2E,4Z)-2,4-decadien-1-ol being a natural flavor component.