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Chapter 31: Q28P. (page 1258)

Crocin, which occurs naturally in crocus and gardenia flowers, is primarily responsible for the color of saffron.

(a) What lipid and monosaccharides are formed by the hydrolysis of crocin?

(b) Classify the lipid as a monoterpenoid, diperpenoid, etc., and locate the isoprene units.

Short Answer

Expert verified

(a) The hydrolysis of crocin is as shown below:

It forms D-glucose (monosaccharide) and the lipid crocetin.

(b) The lipid present in it is crocetin. It is an example of a diterpenoid.

The isoprene units in it are as shown below:

Step by step solution

01

Crocin

The color of saffron is due to crocin. Chemically, crocin is an example of a diester. The carboxylic acid that forms crocin is crocetin and the gentiobiose carbohydrate.

02

Hydrolysis of crocin

The hydrolysis of crocin forms the carbohydrate D-glucose and the dicarboxylic acid crocetin. The products of hydrolysis of crocin are as shown below:

03

The type of lipid present in crocin

The lipid molecule that makes crocin is crocetin. The isoprene units will make the terpenoids. Based on the number of isoprene units, the terpenoid can be classified. In crocin, there are two terpenoids (C5H8) units in it. They are as shown below:

This crocetin is an example of a diterpenoid.

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Most popular questions from this chapter

(a) Draw a skeletal structure of the anabolic steroid methenolone from the following description. Methenolone contains the tetracyclic steroid skeleton with a carbonyl group at C3, a hydroxyl group at C17, a double bond between C1 and C2, and methyl groups bonded to C1, C10 and C13. (b) Add wedges and dashed wedges for all stereogenic centers with the following information: The configuration at C10 is R, The configuration at C13 is S, the configuration at C17 is S, and all substitutents at ring fusions are trans to each other. (c) Draw the structures of Primobolan, the product formed when methenolone is treated with CH3(CH2)5COCl and pyridine. Primobolan is an anabolic steroid that can be taken orally or by injection and has been used illegally by well-known Major League Baseball players.

Write a stepwise mechanism for the following reaction.

(a) Draw a skeletal structure of the anabolic steroid 4-androstene-3, 17-dione, also called “andro,” from the following description. Andro contains the tetracyclic steroid with carbonyl groups at C3 and C17, a double bond between C4 and C5, and methyl groups bonded to C10 and C13.

(b) Add wedges and dashed wedges for all stereogenic centers with the following information: the configuration at C10 is R, the configuration at C13 is S, and all substituents at ring fusions are trans to each other.

Locate the isoprene units in each compound.

(a)(b)

(c)

(d)

(e)(f)

(g)

(h)

Draw the enantiomer and any two diastereomers of cholesterol. Does the OH group of cholesterol occupy an axial or equatorial position?
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