ISOPHYTOL

PRODUCT IDENTIFICATION

CAS NO. 505-32-8

ISOPHYTOL

EINECS NO. 208-008-8
FORMULA C20H40O
MOL WT. 296.54

H.S. CODE

2905.22

TOXICITY

 
SMILES

 

CLASSIFICATION

 

SYNONYMS 3,7,11,15-tetramethylhexadec-1-en-3-ol;
3,7,11,15-Tetramethyl-1-hexadecen-3-ol;

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE clear to yellow oily liquid
MELTING POINT  
BOILING POINT 309 C
SPECIFIC GRAVITY 0.851
SOLUBILITY IN WATER Insoluble
pH  
VAPOR DENSITY  

AUTOIGNITION

 

NFPA RATINGS

Health: 2 Flammability: 1 Reactivity: 0

REFRACTIVE INDEX

1.457

FLASH POINT

175 C

STABILITY Stable under ordinary conditions. Air, light sensitive.

GENERAL DESCRIPTION & APPLICATIONS

Isophytol, an acyclic terpenoid, is used in manufacturing synthetic vitamins E and K. It is also one of ingredient in fragrance. It's end applications include soap, detergent, beauty care product, household product. (Olfactive Note : faint, floral, herbal green.)
SALES SPECIFICATION

APPEARANCE

clear to yellow oily liquid
ASSAY

96.0% max

TRANSPORTATION
PACKING
 
HAZARD CLASS Not regulated
UN NO.  
OTHER INFORMATION
Hazard Symbols: XI, Risk Phrases: 36/37/38, Safety Phrases: 26-37/39 Environmentally hazardous substance

EXTERNAL LINKS

Chemical synthesis. : Total chemical synthesis of isophytol may start from the addition of acetylene (CAS 74–86–2) to acetone (67–64–1) resulting in 3-methyl-1-butyn-3-ol (115–19–5), which is hydrated in the presence of a palladium catalyst to 3-methyl-1-buten-3-ol (115–18–4), which is reacted with either diketene or acetic acid ester to the acetoacetate and the latter thermally reacted to 2-methyl-2-hepten-6-one (110–93–0). Alternatively, 3-methyl-1-buten-3-ol is reacted with isopropenyl methyl ether (116–11–0) to 2-methyl-2-hepten-6-one. In a third synthetic pathway, isoprene hydrochloride is reacted with acetone in the presence of an alkaline condensating agent or in the presence of organic bases as catalysts to 2-methyl-2-hepten-6-one. 2-Methyl-2-hepten-6-one is then reacted with acetylene to dehydrolinalool (29171–20–8), to which isopropenyl methyl ether is added to make pseudoionone (141–10–6). The three double bonds are hydrated to form 6,10-dimethyl-2-undecanone (1604–34–8), which is reacted with acetylene to 3,7,11-trimethyl-1-dodecyn-3-ol (1604–35–9). Isopropenyl methyl ether is added to form 6,10-14-trimethyl-4,5-pentadecadiene-2-one (16647–10–2), which is hydrated to hexahydrofarnesyl acetone (502–69–2). This is again reacted with acetylene to 3,7,11,15-tetramethyl-1-hexadecyn-3-ol (dehydroisophytol, 29171–23–1), which is finally hydrated to isophytol. The repeated addition of acetylene and hydration was first described by Fischer and Löwenberg [1929].

Natural origins.: Isophytol has been reported from several (at least 15) species of flowering plants and from two red algae [various authors, see IUCLID p. 11/133 “Additional Remarks”]. This broad systematic distribution suggests that isophytol is a common compound in plant biochemistry that may have a long evolutionary history. However, no high concentrations have been reported nor is detection truly wide-spread, in contrast to other terpenoid alcohols. The Merck Index [1999] states that isophytol is a "decomposition product of chlorophyll", which would make it a very common substance. However, no literature has been located that would support this statement in the broadly general form used. There is not one single clear identification of isophytol as either a precursor or direct metabolite of chlorophyll; in contrast, the isomer phytol, having the hydroxy group in terminal position, has been shown to be both a precursor and direct metabolite of chlorophyll (and other compounds). On the other hand, for both anaerobic and aerobic, freshwater and marine sediments there is good experimental evidence for abiotic isomerisation of phytol to isophytol [Brooks and Maxwell, 1974; de Leeuw et al., 1977; Didyk etal., 1978; Rontani et al., 1999]. Brooks and Maxwell [1974] commented about this isomerisation of phytol to isophytol through "allylic rearrangement of the hydroxyl function occurring readily" in the context of sediments, probably needing certain clay mineral surfaces for the transformation [deLeeuw et al., 1977]. Further, de Leeuw et al. also showed that this abiotic isophytol is only an early, relatively short-lived intermediate in the diagenetic conversion of chlorophyll-derived phytol to, eventually, kerogen, an insoluble, high-molecular-weight organic constituent of sedimentary (http://www.chem.unep.ch/irptc/)

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