928-96-1 Usage
Description
Leaf alcohol exists as a liquid at room temperature with a characteristic odor of green leaves. It is found in green tea, violet leaf oil, and many types of leaves, herbs, and grasses. Leaf alcohol finds applications in perfumery as floral fragrance. Leaf alcohol is also investigated for its antidiabetic activity.
Chemical Properties
Different sources of media describe the Chemical Properties of 928-96-1 differently. You can refer to the following data:
1. colourless liquid
2. Leaf Alcohol is a colorless
liquid with the characteristic odor of freshly cut grass. In small quantities,
leaf alcohol occurs in the green parts of nearly all plants. The volatile flavor
constituents of green tea contain up to 30%.
A stereospecific synthesis of (Z)-3-hexen-1-ol starts with the ethylation of
sodium acetylide to 1-butyne, which is reacted with ethylene oxide to give
3-hexyn-1-ol. Selective hydrogenation of the triple bond in the presence of
palladium catalysts yields (Z)-3-hexen-1-ol. Biotechnological processes have
been developed for its synthesis as a natural flavor compound, for example.
Leaf alcohol is used to obtain natural green top notes in perfumes and flavors. In
addition, it is the starting material for the synthesis of (2E,6Z)-2,6-nonadien-l-ol
and (2E,6Z)-2,6-nonadien-l-al.
3. cis-3-Hexen-l-ol has an intense, green odor, not as strong as the
corresponding aldehyde and a characteristic herbaceous, leafy
odor on dilution. This substance can be obtained through extraction
from various essential oils and purified by reacting it to the corresponding phthalate or allophanate; it was synthesized by Ruzicka
and Schinz, who also clarified its chemical structure; Stoll and
Rouve reported on the most significant differences between the
natural and the synthetic products.
4. 3-Hexen-1-ol has an intense, grassy-green odor, not as strong as the corresponding aldehyde, and a characteristic herbaceous, leafy odor on dilution.
Occurrence
Main constituent of the oil distilled from the infusion of fermented tea leaves. Reported found as the corresponding ester of phenylacetic acid in the oil of Japanese mint (Mentha arvensis); the volatile oil of Thea chinensis contains
approximately 26 to 35% 3-hexen-1-ol, whereas larger amounts are reported in the oils of Morus bombysic, Robinia pseudacacia and
Raphanus sativus. Probably occurring also in several green leaves and herbs; reported found in the fruit juices of raspberry, grapefruit and others. Also reported in over 200 foods including apple, apricot, banana, citrus peel oils and juices, berries, guava, mango,
grapes, pineapple, cabbage, kohlrabi, celery, cucumber, lettuce, leek, peas, sauerkraut, tomato, ginger, peppermint oil, coconut oil,
spearmint oil, mustard, parsley, breads, butter, fish, fish oil, cognac, brandy, cider, sherry, grape wines, tea, soybeans, avocado,
olive, passion fruit, plum, rose apple, Malay apple, water apple (Syzigium spp.), beans, marjoram, starfruit, broccoli, pear and apple
brandies, figs, brussels sprouts, radish, prickly pear, litchi, dill, lovage, pumpkin, corn oil, malt, laurel, kiwifruit and other sources
Preparation
By the reaction of butyne-1 with ethylene oxide and subsequent selective reduction to the eis isomer (Bedoukian, 1967).
Definition
ChEBI: A primary alcohol that consists of (3Z)-hex-3-ene substituted by a hydroxy group at position 1.
Taste threshold values
Taste characteristics at 30 ppm: fresh, green, raw fruity with a pungent depth
General Description
cis-3-Hexen-1-ol is one of the key volatile constituents of green leaf volatiles(GLV) that can act as an attractant to various insects. It is emitted by green plants when they are physically damaged.
Flammability and Explosibility
Flammable
Synthesis
Extracted from various essential oils and purified by reacting it to the corresponding phthalate or allophanate; it was
synthesized by Ruzi-ka and Schinz, who also clarified its chemical structure; Stoll and Rouve reported on the most significant differences between the natural and the synthetic products (Burdock, 1995)
References
[1] NPCS Board of Consultants & Engineers, Industrial Alcohol of Technology Handbook, 2010
[2] A. Shirwaikar, K. Rajendran and C. Kumar, Oral Antidiabetic Activity of Annona squamosa Leaf Alcohol Extract in NIDDM Rats, Pharmaceutical Biology, 2004, vol. 42, 30-35
Check Digit Verification of cas no
The CAS Registry Mumber 928-96-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,2 and 8 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 928-96:
(5*9)+(4*2)+(3*8)+(2*9)+(1*6)=101
101 % 10 = 1
So 928-96-1 is a valid CAS Registry Number.
928-96-1Relevant articles and documents
Method for synthesizing geraniol from piperylene (by machine translation)
-
Paragraph 0040; 0042-0043, (2020/07/12)
The method comprises the following steps: reacting piperylene with carbon monoxide and hydrogen to prepare an intermediate cis -3 -hexene -1 - aldehyde; and preparing the geraniol through hydrogenation. The yield of the leaf alcohol is 81.56-92 .73percent, the yield of the cis -3 - hexenyl -1 - aldehyde is 80.69-88 .13percent, the yield of the leaf alcohol is -3 - 54.94-80 .35percent (calculated by pentadiene), the yield of the leaf alcohol is 99.2-99 .50percent.1 - percent, and the yield fluctuation range of the leaf alcohol is 10 within 55.53-80 .97percent percent of the yield of the leaf 0.4 alcohol in 98.36-99 .60percent percent. (by machine translation)
Visible light-induced diastereoselective semihydrogenation of alkynes to cis-alkenes over an organically modified titanium(IV) oxide photocatalyst having a metal co-catalyst
Fukui, Makoto,Omori, Yuya,Kitagawa, Shin-ya,Tanaka, Atsuhiro,Hashimoto, Keiji,Kominami, Hiroshi
, p. 36 - 42 (2019/05/04)
Hydrogen (H2)-free and poison (lead and quinoline)-free semihydrogenation of alkynes to cis-alkenes under gentle conditions is one of the challenges to be solved. In this study, a titanium(IV) oxide photocatalyst having two functions (visible light responsiveness and semihydrogenation activity) was prepared by modification with 2,3-dihydroxynaphthalene (DHN) and a copper (Cu) co-catalyst, respectively. The photocatalyst (DHN/TiO2-Cu) showed high performance for diastereoselective semihydrogenation of alkynes to cis-alkenes in water-acetonitrile solution under visible light irradiation without the use of H2 and poisons. Alkynes having reducible functional groups were converted to the corresponding alkenes with the functional groups being preserved. The addition of water to acetonitrile changed the amount of alkynes adsorbed on the photocatalyst, which was a decisive factor determining the rate of hydrogenation. A relatively large apparent activation energy, 27 kJ mol?1, was obtained by a kinetic study, indicating that the rate-determining step of this reaction was not an electron production process but a thermal catalytic semihydrogenation process over the Cu co-catalyst. Semihydrogenation and hydrogen evolution occurred competitively on Cu metals and the former became predominant at slightly elevated temperatures, which is discussed on the basis of the kinetic parameters of two reactions.