Leaf Alcohol

Product Name:

Leaf alcohol

CAS:

928-96-1

MF:

C6H12O

MW:

100.16

EINECS:

213-192-8

Mol File:

928-96-1.mol

Melting point 

22.55°C (estimate)

Boiling point 

156-157 °C(lit.)

density 

0.848 g/mL at 25 °C(lit.)

vapor density 

3.45 (vs air)

refractive index 

n20/D 1.44(lit.)

FEMA 

2563 | CIS-3-HEXENOL

Fp 

112 °F

storage temp. 

Flammables area

form 

Liquid

pka

15.00±0.10(Predicted)

color 

APHA: ≤100

Specific Gravity

0.848 (20/4℃)

Water Solubility 

INSOLUBLE

Merck 

14,4700

JECFA Number

315

BRN 

1719712

Stability:

Stable. Substances to be avoided include strong oxidizing agents and strong acids. Flammable.

CAS DataBase Reference

928-96-1(CAS DataBase Reference)

NIST Chemistry Reference

3-Hexen-1-ol, (Z)-(928-96-1)

EPA Substance Registry System

(Z)-3-Hexen-1-ol (928-96-1)

Hazard Codes 

F

Risk Statements 

10

Safety Statements 

16

RIDADR 

UN 1987 3/PG 3

WGK Germany 

1

RTECS 

MP8400000

F 

10

TSCA 

Yes

HazardClass 

3

PackingGroup 

III

HS Code 

29052990

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

colourless liquid

Chemical Properties

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.

Chemical Properties

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.

Chemical Properties

3-Hexen-1-ol has an intense, grassy-green odor, not as strong as the corresponding aldehyde, and a characteristic her[1]baceous, leafy odor on dilution.

Definition

ChEBI: A primary alcohol that consists of (3Z)-hex-3-ene substituted by a hydroxy group at position 1.

Aroma threshold values

Detection: 70 ppb

Taste threshold values

Taste characteristics at 30 ppm: fresh, green, raw fruity with a pungent depth

Chemical 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 differ[1]ences 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

Preparation Products

CIS-3-HEXENYL BUTYRATE-->FEMA 3498-->TRANS,CIS-2,6-NONADIEN-1-OL-->cis-3-Hexenyl formate-->cis-3-Hexenai-->cis-3-Hexenyl 2-methylbutanoate-->1-HEXEN-3-YL ACETATE-->cfs-3-trans-2-Hexenyl propionate(mixtme)

Raw materials

Sodium-->Ammonia-->Triphenylphosphine-->Litium-->SODIUM ACETYLIDE-->3-HEXYNE-->1-HEXYN-3-OL-->1-BUTYNE