[PCOG-LEC-MID-01-PT5] GLYCOSIDES: ALDEHYDE-PHENOL

THIS FLASH CARDS IS ABOUT GLYCOSIDES; ALDEHYDE-PHENOL (PART 5).

Vanilla

What is the only plant under Aldehyde?

Vanilla

This is a drug that has an aldehydic aglycone as its chief constituent?

Aldehydic aglycone

What is the chief constituent of Vanilla?

Vanillin

The aglycone developed during the curing process.

Curing process

Vanillin is the aglycone developed during what process?

Methylprotocatechuic aldehyde

Vanillin is also known as?

Vanilla

The cured, fully grown but unripe fruit of Vanilla planifolia or from Vanilla fragrans (Orchidaceae).

• Vanilla planifolia; or

• Vanilla fragrans

Vanilla is the cured, fully grown but unripe fruit of?

Orchidaceae

What is the family name of Vanilla (Vanilla planifolia or Vanilla fragrans)?

Mexican/Bourbon Vanilla

Vanilla planifolia is also known as?

Tahiti Vanilla

Vanilla tahitensis is also known as?

Vanilla tahitensis

What is the scientific name of Tahiti Vanilla?

• Glucovanillin (Avenin)

• Glucovanillic alcohol

What are the two (2) constituents of Green Vanilla?

Avenin

The constituent of Green Vanilla, Glucovanillin is also known as?

Glucose + Vanillin

Glucovanillin (Avenin) will be hydrolyzed by an enzyme during the curing process, producing?

Glucose + Vanillic alcohol

Glucovanillic alcohol will be hydrolyzed by an enzyme during the curing process, producing?

Vanillin

The Glucovanillic Alcohol (Glucose + Vanillic Alcohol) will be oxidized into?

Vanillin

This is the principal flavoring constituent.

• 10% sugar

• 10% fixed oil

• Calcium oxalate

Vanilla is made up of?

• Flavoring agent

• Pharmaceutic acid

• Source of vanillin

• Ethyl vanillin

What are the four (4) uses of vanilla?

Vanilla Tincture

Vanilla can be used in this as a flavoring agent.

Flavoring agent

Vanilla in vanilla tincture is used as?

Vanilla

This is a source of vanillin.

Synthetically

We can obtain from vanilla, but it can also be prepared?

• Coniferin

• Eugenol

• Lignin

What are the three (3) ways of obtaining vanilla synthetically?

Coniferin

OBTAINING VANILLA SYNTHETICALLY

Glycoside present in cambium sap of pine tree.

Glycoside

What is present in Coniferin?

Cambium Sap of Pine Tree

In Coniferin, Glycoside is present in the?

Eugenol

OBTAINING VANILLA SYNTHETICALLY

Phenol present in clove oil.

Phenol

What is present in Eugenol?

Clove Oil

In Eugenol, Phenol is present in?

Lignin

OBTAINING VANILLA SYNTHETICALLY

This is a product of pulp industry.

Pulp Industry

Lignin is the product of?

Ethyl vanillin

The synthetic analog of vanillin.

Lactone

This glycoside has lactone ring; carbon-oxygen bond with a ring structure.

• Coumarin

• Cantharides

• Psoralens

What are the three (3) substances under Lactone?

• Ferric chloride Test

• Fluorescence Test

What are the two (2) chemical tests of Lactone?

Ferric chloride Test

This chemical test of Lactone, results in positive (+) deep green color, which turns yellow upon addition of concentrated Nitric acid.

Positive (+) deep green color

In ferric chloride test of lactone, it results in ___________ which turns yellow upon addition of concentrated Nitric acid.

Yellow

In ferric chloride test of lactone, the positive (+) deep green color turns what color upon addition of concentrated Nitric acid?

Concentrated Nitric Acid

In ferric chloride test of lactone, the positive (+) deep green color turns yellow upon addition of?

Fluorescence Test

This chemical test of Lactone, results in positive (+) blue-green fluorescence.

Positive (+) blue-green fluorescence

In fluorescence test of lactone, it results in?

Coumarin

What was the first lactone glycoside?

Coumarin

This substance of lactone is a lactone of o-hydroxycinnamic acid and is found notably in high concentration in tonka bean (Dipteryx odorata, Leguminosae), woodruff and sweet vernal grass (Antoxanthum odoratum, Graminae).

O-hydroxycinnamic acid

Coumarin is a lactone of?

• Tonka Bean

• Woodruff and Sweet vernal grass

Coumarin is a lactone of o-hydroxycinnamic acid and is found notably in high concentration in?

Dipteryx odorata

What is the scientific name of Tonka Bean?

Tonka Bean

Dipteryx odorata is the scientific name of?

Leguminosae

What is the family name of Tonka Bean (Dipteryx odorata)?

Antoxanthum odoratum

What is the scientific name of Woodruff and Sweet Vernal Grass?

Woodruff and Sweet Vernal Grass

Antoxanthum odoratum is the scientific name of?

Graminae

What is the family name of Woodruff and Sweet Vernal Grass (Antoxanthum odoratum)?

• Colorless, prismatic crystals

• Fragrant smell

• Bitter, aromatic burning taste

• Soluble in alcohol

What are the four (4) characteristics of Coumarin?

False — Coumarin is soluble in alcohol.

True or False: Coumarin is insoluble in alcohol.

Flavoring agents

What is the use of Coumarin that is no longer being used because of Coumarin-drug interactions?

Dicumarol

This derivative of coumarin is obtained originally from improperly cured leaves and flowering tops of Melilotus officinalis (Leguminosae) but now prepared synthetically.

Bishydroxycoumarin

Dicumarol is also known as?

Dicumarol (Bishydroxycoumarin)

What is the first oral anticoagulant?

Melilotus officinalis

Dicumarol is obtained originally from improperly cured leaves and flowering tops of?

Leguminosae

What is the family name of Melilotus officinalis?

True

True or False: Dicumarol is now prepared synthetically.

25-200 mg once a day

What is the initial dose of Dicumarol?

200-300 mg

What is the maximum dose of Dicumarol?

Warfarin and other anticoagulant drugs

Dicumarol can be a precursor for?

Cantharides

This substance of lactone consists of the dried insect Cantharis vesicatoria (Meloidae).

Cantharis vesicatoria

Cantharides consists of the dried insect called?

Spanish / Russian / Blistering Flies

Cantharis vesicatoria is also known as?

Meloidae

What is the family name of Spanish/Russian/Blistering Flies (Cantharis vesicatoria)?

1. Mature insect

2. Reagents

3. Drying

4. Storage

5. Preserve

What are the five (5) steps in preparing Cantharides?

Mnemonics: Mr. DSP

Brilliant green with metallic luster

Step 1: Mature Insect

What are the physical attributes of mature insect used in the preparation of cantharides?

• Plunge: dilute in acetic acid or dilute vinegar

• Fumes: hot vinegar, NH₄, CCl₄, Sulfur dioxide

Step 2: Reagents

The mature insect will be killed using what different reagents?

• Dilute in acetic acid

• Dilute vinegar

What are the reagents (plunge) used in killing the mature insects in step 2?

• Hot vinegar

• Ammonia (NH₄)

• Carbon tetrachloride (CCl₄)

• Sulfur dioxide

What are the four (4) reagents (fumes) used in killing mature insects in step 2?

Not more than 40 degrees celsius

Step 3: Drying

What is the desired temperature in drying the killed matured insects?

Tight container

Step 4: Storage

Where is the dried killed matured insects stored?

• Chloroform; or

• Tetrachloride

Step 5: Preserve

The dried killed matured insects stored in tight storage will be preserved using a few drops of?

• Rubefacient

• Irritant

• Vesicant

• Aphrodisiac

• Warts removal

What are the five (5) uses of Cantharides?

Mnemonics: RIVAW

Rubefacient

This use of cantharides is for muscle/joint pain.

Vesicant

This use of cantharides is for blisters or tissue damage.

Aphrodisiac

This use of cantharides is taken internally and excreted by kidney which can irritate the urinary tract.

Priapism

This results to the irritation of the urinary tract with a prolonged and painful erection because of aphrodisiac.

• Cantharidin (chief principal constituent)

• Fat (12%)

What are the two (2) constituents of cantharides?

Cantharidin

What is the chief principal constituent of cantharides?

12%

As the constitute of cantharides, what is the % of fat in it?

0.7% cantharidin

For warts removal, what is the % of cantharidin?

Psoralens

This substance of lactone is a photosensitizing furocoumarins that occur in a number of plant families, including the Umbelliferae, where they are a common cause of phototoxicity.

Photosensitizing furocoumarins

Psoralens in a?

Umbelliferae

Psoralens is a photosensitizing furocoumarins that occur in a number of plant families, including the?

Psoralens

This substance of lactone are a common cause of phototoxicity.

Phototoxicity

Psoralens are a common cause of?

Ammi majus

Psoralens is the fruit of?

• Bishop’s flower

• Bishop’s weed

What are the other/common names of Ammi majus?

Umbelliferae

What is the family name of Ammi majus?

• Methoxsalen

• Trioxsalen

What are the constituents of psoralens?

Methoxsalen

Facilitate repigmentation in idiopathic vitiligo; symptomatic control of severe, disabling psoriasis.

Repigmentation

Psoralens facilitates ______ in idiopathic vitiligo.

Idiopathic vitiligo

Psoralens facilitates repigmentation in ___________ (autoimmune disease, destroyed melanocytes)?

Severe, disabling psoriasis

Psoralens is a symptomatic control of?

• 8-methoxypsoralen

• Xanthotoxin

What are the other two (2) names of psoralens?