AMBRAIN Chemical Properties

FEMA 

2608 | LABDANUM ABSOLUTE (CISTUS SPP.)

Odor

at 10.00 % in dipropylene glycol. woody old wood burnt wood ambergris animal phenolic smoky balsamic cedar

Odor Type

woody

EPA Substance Registry System

Oils, labdanum (8016-26-0)

Safety Information

Hazard Codes 

Xi

Risk Statements 

38

Safety Statements 

26-36

Toxicity

The acute oral LD₅₀ value in rats was reported as 8.98 g/kg (5.40-12.56 g/kg) (Hart, 1971). The acute dermal LD₅₀ value in rabbits exceeded 5 g/kg

AMBRAIN Usage And Synthesis

Description

Refer to LABDANUM, ABSOLUTE.

Chemical Properties

Shrubs growing in thickets in several Mediterranean islands (Crete, Cyprus) and countries (Spain particularly). In the Spanish region of Zamora, C. ladaniferus L. and its varieties-C. albiflorus Dun., C. stenophyllus Dun.t C. maculatus D un-are predominant. On the other hand, the extractive use of C. creticus growing on the island of Crete is steadily decreasing.
Labdanum resin consists of the secretion of the glandular hairs covering the inferior part of the leaves (spring and summer). The hairy leaves and twigs are treated with boiling water, and the floating resin is skimmed from the surface. Crude labdanum resin is a dark brown, semisolid mass with a very pleasant, balsamic odor reminiscent of ambergris and a bitter taste.
In the past, the resin was harvested by using a special whip (con sisting of several leather strips) to flog the plant. The leather strips would become impregnated with the gum resin, which was sub sequently shaved off with special blades. This method is no longer used. To prepare a colorless product, the crude resin can be extracted with filtered ligroin, and finally the solvent is evaporated.
The parts used are the leaves and twigs from which the gum resin is removed. The gum resin is used to prepare derivatives. The organoleptic characteristic of labdanum is a sweet, herbaceous, balsamic odor reminiscent of ambergris with a rich, lasting, ani mal-like undertone.
The essential oil, obtained by steam distillation of the crude gum resin, is a bright-yellow liquid that turns brown with age. It has a strong, balsamic odor reminiscent of ambergris on dilution. Phys ical-chemical constants of the oil follow:An essential oil, called cistus oil, is also steam distilled directly from the dried leaves and twigs. This oil is a pale-orange liquid with a characteristic herbaceous odor reminiscent of camomile.
The main constituents that have been identified in labdanum oil are terpenes, benzaldehyde, acetophenone, a ketone with a pep permint odor, acetic acid, and eugenol.
The derivatives are concrete, absolute, and resinoid and resin abso lute.
Concrete: The concrete is prepared by hydrocarbon extraction of dried (in the shade) and comminuted leaves and twigs. It is a dark green mass with a pleasant balsamic, herbaceous odor. The phys ical-chemical constants vary widely, depending on the source.

Chemical Properties

Prepared by alcoholic extraction of the concrete in approximately 55 to 60% yields. The absolute consists of a semisolid, olive-green mass with a characteristic ambergris odor

Chemical Properties

Shrubs growing in thickets in several Mediterranean islands (Crete, Cyprus) and countries (Spain, particularly). In the Spanish region of Zamora, C. ladanifer L. and its varieties are predominant. On the other hand, the extractive use of C. creticus growing on the island of Crete is steadily decreasing. The part used is resin gum from leaves and twigs. Labdanum has a sweet, herbaceous, balsamic odor reminiscent of ambergris with a rich, lasting, animal-like undertone

Chemical Properties

The oil, obtained by steam distillation of the crude gum resin, is a bright-yellow liquid that turns brown with age. It has a strong, balsamic odor reminiscent of ambergris on dilution. There is also an oil called cistus oil, which is steam-distilled directly from the dried leaves and twigs. The oil has a characteristic herbaceous odor reminiscent of chamomile

Chemical Properties

Labdanum absolute is produced by extraction of the gum with alcohol (e.g., methanol or ethanol). The so-called colorless absolutes are obtained from absolutes by extraction with, for example, hexane.
Steam distillation of the gum yields labdanum oil, which is a golden yellow, viscous liquid that quickly turns dark brown on standing:
d²⁵₂₅ 0.905–0.993; n²⁰_D 1.4920–1.5070; α²⁰_D +0°15′to +7°, often difficult to determine due to its dark color; solubility: 1 vol in 0.5 vol of 90% ethanol, solutions frequently opalescent to turbid, paraffinsmay separate upon further dilution; acid number: 18–86; ester number: 31–86.
Cistus oil and extracts are products with completely different sensory properties. They are derived from the leaves and young twigs of C. ladanifer. Cistus oil is obtained by steam distillation; solvent extraction yields cistus concrete. Cistus oil, in contrast to labdanum oil, consists mainly of monoterpene hydrocarbons.
Cistus and labdanum products are produced in some Mediterranean countries (Spain, France,Morocco), where the Cistus shrub grows abundantly.They are used in perfumery, giving perfume compositions awarm, balsamic tonalitywith a touch of ambergris. The typical odor originates from a number of compounds that are formed by oxidative degradation of diterpenes with the labdane skeleton, which are the main constituents of labdanum gum. The resinoids and absolutes are excellent natural fixatives.

Occurrence

Found in the gum of the shrub Cistus ladaniferus L

Preparation

By steam distillation of the crude gum

Definition

Extractives and their physically modified derivatives. Cistus ladaniferus, Cistaceae.

Essential oil composition

The main constituents of the oil include terpenes, benzaldehyde, acetophenone, a ketone with a peppermint odor, acetic acid and eugenol.

Essential oil composition

The oil contains α-pinene (3.5%), camphene (11%), limonene (2.6%), γ-terpinene (2%), bornyl acetate (4.2%), α-thujone (0.8%), carophylline (0.47%), δ-phellandrene (0.41%), linalool (0.5%), eucalyptol (0.2%), cadinene (0.3%), benzaldehyde, myrcene, p-cymene (4%), eugenol (trace). Levels of some components vary depending on the harvesting time (CoE, 2000). Also see Labdanum oil.

AMBRAIN(8016-26-0)Related Product Information

• TRIS(2,2,6,6-TETRAMETHYL-3,5-HEPTANEDIONATO)EUROPIUM(III)
• Tris(2,4-pentanedionato)chroMiuM(III)
• TERT-BUTYL ISOCYANIDE
• 2,4-PENTANEDIONE, SILVER DERIVATIVE
• METHYL ISOCYANOACETATE
• DICHLORO(ETHYLENEDIAMINE)PLATINUM(II)
• SALCOMINE
• Ethyl isocyanoacetate
• COBALT(II) ACETYLACETONATE
• Aluminum acetylacetonate
• PHENYLSELENOL
• Ferric acetylacetonate
• N-BUTYLISOCYANIDE
• Benzyl isocyanide
• TRIS(2,2,6,6-TETRAMETHYL-3,5-HEPTANEDIONATO)DYSPROSIUM(III)
• Cupric acetylacetonate
• 1,1,3,3-TETRAMETHYLBUTYL ISOCYANIDE
• Tosylmethyl isocyanide