59121-99-2

Basic information

• Product Name: (4E,6E)-3,7,11-trimethyldodeca-1,4,6,10-tetraen-3-ol
• Synonyms: (4E,6E)-3,7,11-Trimethyl-1,4,6,10-dodecatetraen-3-ol; (4E,6E)-3,7,11-Trimethyldodeca-1,4,6,10-tetraen-3-ol; 1,4,6,10-dodecatetraen-3-ol, 3,7,11-trimethyl-, (4E,6E)-; 125474-34-2; 423-240-1
• CAS NO: 59121-99-2
• Molecular Formula: C₁₅H₂₄O
• Molecular Weight: 220.3505
• EINECS: 423-240-1
• Mol File: 59121-99-2.mol

Chemical Properties

• Boiling Point: 320.539°C at 760 mmHg
• Flash Point: 115.687°C
• Density: 0.884g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.495
• PKA: 13.51±0.29(Predicted)
• CAS DataBase Reference: (4E,6E)-3,7,11-trimethyldodeca-1,4,6,10-tetraen-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (4E,6E)-3,7,11-trimethyldodeca-1,4,6,10-tetraen-3-ol(59121-99-2)
• EPA Substance Registry System: (4E,6E)-3,7,11-trimethyldodeca-1,4,6,10-tetraen-3-ol(59121-99-2)

Safety Data

• Hazardous Substances Data: 59121-99-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(4E,6E)-3,7,11-trimethyldodeca-1,4,6,10-tetraen-3-ol is used as a precursor for the synthesis of vitamin E, which is an essential nutrient with antioxidant properties that helps protect cells from damage.
Used in Antioxidant Applications:
(4E,6E)-3,7,11-trimethyldodeca-1,4,6,10-tetraen-3-ol is used as an antioxidant due to its potential antioxidant properties, which can help protect cells from damage caused by free radicals.
Used in Anti-inflammatory Applications:
(4E,6E)-3,7,11-trimethyldodeca-1,4,6,10-tetraen-3-ol is used as an anti-inflammatory agent due to its potential anti-inflammatory properties, which can help reduce inflammation and swelling.
Used in Cancer Treatment:
(4E,6E)-3,7,11-trimethyldodeca-1,4,6,10-tetraen-3-ol is used in the treatment of certain types of cancer due to its ability to induce apoptosis in cancer cells, which can help inhibit tumor growth and progression.

Upstream product

• 58689-15-9 pseudoionone 
• 20082-23-9 (4E,6E/Z)-3,7,11-Trimethyldodeca-4,6,10-trien-1-yn-3-ol 
• 141-10-6 pseudoionone 
• 71570-25-7 (E)-1-iodo-2,6-dimethyl-hepta-1,5-diene 
• 22842-10-0 2-methylhept-2-en-6-yne 
• 106-24-1 Geraniol 
• 141-27-5 3,7-dimethyl-2,6-octadienal 
• 1826-67-1 vinyl magnesium bromide 
• 145571-82-0 (all-E)-3,7,11-Trimethyldodeca-4,6,10-trien-1-yn-3-ol 

Downstream Products

• 103956-99-6 (2E,4E,6E,8E,10E,12E,14E)-2,7,11,15,19-pentamethylicosa-2,4,6,8,10,12,14,18-octaenal 
• 502-65-8 (5Z,5'Z)-Lycopene 
• 131801-83-7 [3,7,11-trimethyl-dodecyl-2,4,6,10-tetraenyl]-triphenylphosphonium chloride 
• 131801-85-9 (2E,4E,6Z)-3,7,11-trimethyldodeca-2,4,6,10-tetraen-1-yl-triphenylphosphonium chloride 

Relevant articles and documents

Synthesis of conjugated trienes and related oxidation products of α-farnesene

The synthesis of conjugated trienes and related oxidation products of α-farnesene (1), principally from the epoxides of α-farnesene (1), is reported. Base-promoted ring opening of 6,7-epoxide (4) by KOBut/LiNPri2 affords the conjugated triene (2), whilst the 3,4-epoxide (5) affords trienol (7). In contrast, 10,11-epoxide (6) fails to undergo epoxide ring opening; it rearranges to the conjugated triene epoxide (8). Base-promoted ring opening of bisepoxide (9) afforded trienol epoxide (11) at -30°C, whilst cyclization to tetrahydrofurans (10a,b) occurred at room temperature. Photosensitized oxidation of 10,11-epoxide (6) followed by in situ treatment with acid gave the cyclic peroxide (3) and on reduction triol (12). Bisallylic alcohol (13) was prepared by alkylation of 3-methylsulfolene with geranial. Trienes (2) and (3) have been isolated previously as autoxidation products of α-farnesene (1) and are implicated as the causal agents of superficial scald of stored apples.

Synthesis of sesquiterpene polyene hydroperoxides by regio- and stereoselective transposition reactions

Isomeric unsaturated alcohols (8), (16), (18) and (20), on exposure to hydrogen peroxide or water in the presence of an acid catalyst, undergo exceptionally regio- and stereoselective substitution reactions to form hydroperoxide (3) and alcohol (8) respectively. E/Z isomeric ratios of transposition products indicate that the intermediate acyclic carbocations (21) and (22) are not interconverting under the reaction conditions. Practical syntheses of α-farnesene autoxidation products have been developed based on these transposition reactions.

Synthesis, Isolation, and NMR-Spectroscopic Characterization of Fourteen (Z)-Isomers of Lycopene and of Some Acetylenic Didehydro- and Tetradehydrolycopenes

Eight (Z)-isomers of lycopene were prepared by stereocontrolled syntheses and fully characterized by 1H-NMR, 13C-NMR, mass, and UV/VIS-spectroscopy: (5Z)-, (7Z)-, (15Z)-, (5Z,5'Z)-, (7Z,7'Z)-, (7Z,9Z)-, (9Z,9'Z)-, and (7Z,9Z,7'Z,9'Z)-lycopene.Six additional (Z)-isomers, namely (9Z)-, (13Z)-, (5Z,9'Z)-, (9Z,13'Z)-, (5Z,9Z,5'Z)-, and (5Z,13Z,5'Z)-lycopene, were isolated in small quantities from isomer mixtures by semiprep.HPLC and were identified by 1H-NMR spectroscopy.

The Stereoselective Synthesis of α,β-Unsaturated Ketones by the Stepwise Cross-Coupling Reaction of -(2-Bromoethenyl)diisopropoxyborane

The palladium catalyzed stepwise cross-coupling reaction of (E)-(2-bromoethenyl)diisopropoxyborane, readily available by bromoboration of acetylene, with α-alkoxyalkenylzinc chlorides and organic halides gives α,β-unsaturated ketones in good yields with high (E)-selectivity.

Manufacture of symmetrical carotenoids

Symmetrical carotenoids are prepared from the half-molecules by dimerizing the phosphonium salts of the half-molecules with peroxides, peroxo compounds or peroxy compounds in an alkaline medium.