“Isophytol”的意思、由来-开放百科全书

词条

Isophytol

释义

Occurrence
Synthesis
Uses
Toxicology
See also
References
Bibliography

{{Chembox
| ImageFile = Isophytol.svg
| ImageSize = 200px
| ImageAlt =
| IUPACName = 3,7,11,15-Tetramethylhexadec-1-en-3-ol
| OtherNames =
| Section1 = {{Chembox Identifiers
| CASNo = 505-32-8
| EINECS = 208-008-8
| PubChem = 10453
| SMILES = CC(C)CCCC(C)CCCC(C)CCCC(C)(C=C)O
| InChI=1S/C20H40O/c1-7-20(6,21)16-10-15-19(5)14-9-13-18(4)12-8-11-17(2)3/h7,17-19,21H,1,8-16H2,2-6H3
| Section2 = {{Chembox Properties
| C = 20
| H = 40
| O = 1
| MolarMass =
| Appearance = Colorless viscous liquid
| Density = 0.8458 g/cm³ (20 ºC)
| MeltingPt =
| BoilingPtC = 334.88
| Solubility = Poor
| Solvent = other solvents
| SolubleOther = Very soluble in benzene, diethyl ether, and ethanol
| Section3 = {{Chembox Hazards
| MainHazards =
| AutoignitionPt =
| GHSPictograms = {{GHS07}}{{GHS09}}
| PPhrases = {{P-phrases|264|273|280|302+352|321|332+313|362|391|501}}
| FlashPtC = 135
| FlashPt_notes = (closed cup)
}}

Isophytol is a terpenoid alcohol that is used as a fragrance and as an intermediate in the production of vitamin E and K₁.^[1]{{sfn|OECD|2003|p=6}}

Occurrence

Isophytol has been in found in two red algae species and more than 15 plant species. Concentrations found have been low.{{sfn|OECD|2003|p = 7}}

Synthesis

It can be synthesized in six steps from pseudoionone and propargyl alcohol.^[2] Total synthesis begins with the combination of acetylene and acetone to produce 3-methyl-1-butyn-3-ol. Hydrogenation by palladium catalysis results in 3-methyl-1-buten-3-ol. Reaction with diketene or acetic acid ester creates the acetoacetate; thermal reaction leads to 2-methyl-2-hepten-6-one. The steps of adding acetylene and then isopropenyl methyl ether and hydrogenating the product are done twice (this involves an intermediate of pseudoionone); then acetylene is added to create dehydroisophytol. Hydrogenation results in isophytol.{{sfn|OECD|2003|p = 7}}

Uses

Production industrially was estimated to be 35000 to 40000 tons in 2002,{{sfn|OECD|2003|p = 45}} created by total synthesis, with about 99.9% used in synthesizing vitamin E and vitamin K₁. More than 95% of the less than 40 tons used annually in consumer products is as a fragrance. Less than 2 tons a year is used for flavoring.{{sfn|OECD|2003|p = 22}}

In perfumes the concentration is 0.2% v/v at most.{{sfn|OECD|2003|p = 12}}

Toxicology

Oral {{LD50}} values in mammals are greater than 5000 mg/kg.{{sfn|OECD|2003|p = 3}}

References

1. ^{{cite journal|last1=McGinty|first1=D.|last2=Letizia|first2=C.S.|last3=Api|first3=A.M.|title=Fragrance material review on isophytol|journal=Food and Chemical Toxicology|date=January 2010|volume=48|pages=S76–S81|doi=10.1016/j.fct.2009.11.015|pmid=20141882|url=https://www.sciencedirect.com/science/article/pii/S0278691509005316|language=en|issn=0278-6915}}
2. ^{{cite journal|last1=Sato|first1=Kikumasa|last2=Kurihara|first2=Yoshie|last3=Abe|first3=Shigehiro|title=Synthesis of Isophytol|journal=The Journal of Organic Chemistry|date=January 1963|volume=28|issue=1|pages=45–47|doi=10.1021/jo01036a009}}

Bibliography

{{cite report||url = http://www.chem.unep.ch:80/irptc/sids/OECDSIDS/505328.pdf|archive-url = https://web.archive.org/web/20120328182240/http://www.chem.unep.ch:80/irptc/sids/OECDSIDS/505328.pdf|dead-url = yes|archive-date = 2012-03-28|author = OECD|publisher = UNEP|title = Isophytol SIDS Initial Assessment Report for SIAM 16|date = 21 February 2003|ref = harv}}

3 : Tertiary alcohols|Diterpenes|Fatty alcohols

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