13920-14-4

Basic information

• Product Name: 15-cis-7,7',8,8',11,11',12,12'-octahydro-psi.psi-Carotene
• Synonyms: 15-cis-7,7',8,8',11,11',12,12'-octahydro-psi.psi-Carotene;prephytoene diphosphate;15-cis-7,7',8,8',11,11',12,12'-Octahydro-lycopene;15-cis-7,7',8,8',11,11',12,12'-Octahydro-ψ,ψ-carotene;15-cis-Phytoene (90%);PhytoflORAL
• CAS NO: 13920-14-4
• Molecular Formula: C₄₀H₆₄
• Molecular Weight: 544.93616
• Product Categories: Aliphatics
• Mol File: 13920-14-4.mol

Chemical Properties

• Boiling Point: 620.3°Cat760mmHg
• Flash Point: 333°C
• Appearance: /
• Density: 0.865g/cm³
• Storage Temp.: Amber Vial, -86°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Stability: Light Sensitive, Temperature Sensitive
• CAS DataBase Reference: 15-cis-7,7',8,8',11,11',12,12'-octahydro-psi.psi-Carotene(CAS DataBase Reference)
• NIST Chemistry Reference: 15-cis-7,7',8,8',11,11',12,12'-octahydro-psi.psi-Carotene(13920-14-4)
• EPA Substance Registry System: 15-cis-7,7',8,8',11,11',12,12'-octahydro-psi.psi-Carotene(13920-14-4)

Safety Data

• Hazardous Substances Data: 13920-14-4(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
15-cis-7,7',8,8',11,11',12,12'-octahydro-psi.psi-Carotene is used as an intermediate for the production of carotenoids, which are essential for various biological functions and have significant health benefits. These carotenoids are used in the development of pharmaceutical products that target specific health conditions.
2. Used in Nutraceutical Industry:
In the nutraceutical industry, 15-cis-7,7',8,8',11,11',12,12'-octahydro-psi.psi-Carotene is used as a key component in the synthesis of carotenoids that are added to dietary supplements and functional foods. These carotenoids contribute to the overall health and well-being of consumers by providing essential nutrients and supporting various physiological processes.
3. Used in Cosmetic Industry:
15-cis-7,7',8,8',11,11',12,12'-octahydro-psi.psi-Carotene is also utilized in the cosmetic industry as a natural colorant and antioxidant. Its clear, colorless oil form makes it an ideal ingredient for various cosmetic products, such as creams, lotions, and serums, where it helps to maintain the product's stability and enhance its appearance.
4. Used in Agricultural Industry:
In agriculture, 15-cis-7,7',8,8',11,11',12,12'-octahydro-psi.psi-Carotene is used as a precursor in the production of carotenoids that are essential for the natural coloration and health of plants. These carotenoids can be applied to crops to improve their nutritional value and enhance their resistance to various environmental stresses.
5. Used in Food Industry:
The food industry utilizes 15-cis-7,7',8,8',11,11',12,12'-octahydro-psi.psi-Carotene as a natural colorant and antioxidant in the production of various food products. Its clear, colorless oil form allows for easy incorporation into a wide range of products, such as beverages, snacks, and ready-to-eat meals, where it helps to maintain freshness and improve the overall quality of the products.

Synthetic route

2E,6E,10E-geranylgeranyl aldehyde (13920-11-1, 32480-11-8, 57784-38-0, 58188-09-3, 132513-59-8, 13920-12-2) + triphenyl-((2E,6E,10E)-3,7,11,15-tetramethyl-hexadeca-2,6,10,14-tetraenyl)-phosphonium; bromide (57784-37-9) → phytofluene (13920-14-4)

Conditions	Yield
With ethyloxirane

hydroxy lycopersene → phytofluene (13920-14-4) + phytoene (540-04-5)

Conditions	Yield
With aluminum oxide for 3h;	A 4 mg B 2 mg

acetoxy lycopersene → phytofluene (13920-14-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 7 mg / LiAlH4 / diethyl ether 2: 4 mg / Al2O3 / 3 h View Scheme

6,10,14-trimethyl-5,9,13-pentadecatriene-2-on (1117-52-8) → phytofluene (13920-14-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: NaOMe, MeOH / dimethylformamide 2: LiAlH4 / diethyl ether 3: Ag2CO3-celite / benzene 4: ethyloxirane View Scheme

Geranylgeraniol (24034-73-9) → phytofluene (13920-14-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: Ag2CO3-celite / benzene 2: ethyloxirane View Scheme

(2E,6E,10E)-methyl 3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenoate (42207-88-5) → phytofluene (13920-14-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: LiAlH4 / diethyl ether 2: Ag2CO3-celite / benzene 3: ethyloxirane View Scheme

tetrachloromethane (56-23-5) + N-Bromosuccinimide (128-08-5) + phytofluene (13920-14-4) + acetic acid (64-19-7) → 15-cis-phytofluene (27664-65-9) + all-(E)-phytofluene (540-05-6)

Conditions	Yield
at 40℃;

phytofluene (13920-14-4) → all-(E)-phytofluene (540-05-6)

Conditions	Yield
With tetrachloromethane; N-Bromosuccinimide; acetic acid

phytofluene (13920-14-4) → 2,6,10,14,19,23,27,31-octamethyldotriacontane (45316-02-7)

Conditions	Yield
With platinum Hydrogenation;

phytofluene (13920-14-4) + p-benzoquinone (106-51-4) → 15-cis-phytofluene (27664-65-9) + all-(E)-phytofluene (540-05-6)

Conditions	Yield
at 130℃;

Upstream product

• 13920-11-1 2E,6E,10E-geranylgeranyl aldehyde 
• 57784-37-9 triphenyl-((2E,6E,10E)-3,7,11,15-tetramethyl-hexadeca-2,6,10,14-tetraenyl)-phosphonium; bromide 
• 1117-52-8 6,10,14-trimethyl-5,9,13-pentadecatriene-2-on 
• 24034-73-9 Geranylgeraniol 
• 42207-88-5 (2E,6E,10E)-methyl 3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenoate 
• 38818-91-6 (((2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl)sulfonyl)benzene 
• 116059-44-0 ((6E,10E,14E,16Z,18E,22E,26E)-2,6,10,14,19,23,27,31-Octamethyl-dotriaconta-2,6,10,14,16,18,22,26,30-nonaene-16-sulfonyl)-benzene 
• 116059-54-2 (6E,10E,14E,18E,22E,26E)-17-Benzenesulfonyl-2,6,10,14,19,23,27,31-octamethyl-dotriaconta-2,6,10,14,18,22,26,30-octaen-16-ol 
• 93040-98-3 all-E 3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentanenal 
• 116059-40-6 Acetic acid (3E,7E,11E)-2-benzenesulfonyl-4,8,12,16-tetramethyl-1-((1E,5E,9E)-2,6,10,14-tetramethyl-pentadeca-1,5,9,13-tetraenyl)-heptadeca-3,7,11,15-tetraenyl ester 

Downstream Products

• 27664-65-9 15-cis-phytofluene 
• 540-05-6 all-(E)-phytofluene 

Relevant articles and documents

POLYPRENOLS AND HYDROXYLATED LYCOPERSENES FROM MYRIOPHYLLUM VERTICILLATUM

Key Word Index-Myriophyllum verticillatum; Haloragaceae; terpenoids; polyprenols; hydroxy lycopersene; iso-hydroxy lycopersene.In a chemical investigation of the aquatic plant Myriophyllum verticillatum three polyprenols and two monohydroxy lycopersenes have been characterized on the basis of their chemical and physical features.The novel compounds hydroxy lycopersene and iso-hydroxy lycopersene may be easily included in the carotenoid biosynthetic pathway.

METHOD FOR THE PRODUCTION OF PHYTOFLUENE

The invention relates to a method for the production of phytofluene of formula I, where a) a phosphonium salt of formula II is condensed with an aldehyde of formula III to give an acetal of formula IV in a Wittig reaction, b) the condensation product of formula IV undergoes an acid-catalysed acetal hydrolysis to give the aldehyde of formula V and c) V is condensed with a phosphonium salt of formula VI to give phytofluene in a further Wittig reaction, whereby the groups R1, R2, R7, X- and Y- have the meanings given in the description.

Formation of symmetrical alkenes by homocoupling of metallated sulfones under nickel catalysis

Summary -Allylic sulfones undergo a coupling reaction with organometallic compounds (Mg or Li) not only with copper catalysts but also with iron or nickel salts. With 7,7-disubstituted allylic sulfones and also saturated aliphatic sulfones, however, another reaction was observed whereby two molecules of the starting sulfone are coupled to give symmetrical alkenes. The scope of this reaction was investigated. Elsevier.

Syntheses with Sulfones L : Preparation of β-Hydroxysulfones through the Combined Oxidative Desulfonylation/Condensation Reaction of Sulfonyl Anions. Application to Terpene Synthesis.

The oxidative desulfonylation of primary sulfonyl anions with the molybdenum peroxide reagent, MoO5.Py.HMPA, leads directly to β-hydroxysulfones through condensation of the starting α-sulfonyl anion with the aldehyde formed in situ.Symmetrical polyenes such as (Z)-12-dehydrosqualene and (Z)-16-phytoene have been obtained in three steps in > 87percent stereoslectivity from the corresponding β-hydroxysulfones.

Synthese d'olefines et de polyenes par doublement d'anions α-sulfonyles en presence de sels de nickel

The lithium or magnesium derivatives of allyl, benzyl and alkyl sulphones are converted efficiently by a catalytic amount of nickel(II) acetylacetonate into symmetrical olefins in THF at 60 deg C.Thus, phytoene was obtained in a 70percent yield from geranylgeranylsulphone.