538368-86-4

Basic information

• Product Name: (3R,4S)-3,4-bis (benzoyloxy) dihydro-2(3H)- Furanone
• Synonyms: (3R,4S)-3,4-bis (benzoyloxy) dihydro-2(3H)- Furanone
• CAS NO: 538368-86-4
• Molecular Formula: C₁₈H₁₄O₆
• Molecular Weight: 326.30016
• Mol File: 538368-86-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3R,4S)-3,4-bis (benzoyloxy) dihydro-2(3H)- Furanone(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S)-3,4-bis (benzoyloxy) dihydro-2(3H)- Furanone(538368-86-4)
• EPA Substance Registry System: (3R,4S)-3,4-bis (benzoyloxy) dihydro-2(3H)- Furanone(538368-86-4)

Safety Data

• Hazardous Substances Data: 538368-86-4(Hazardous Substances Data)

Usage

Description

(3R,4S)-3,4-bis (benzoyloxy) dihydro-2(3H)-Furanone, also known as r-butyrolactone and strawberry lactone, is a chemical compound characterized by its strong strawberry aroma. It is a versatile ingredient used across various industries due to its distinct fragrance and flavor.

Uses

Used in Food Industry:
(3R,4S)-3,4-bis (benzoyloxy) dihydro-2(3H)-Furanone is used as a flavoring agent for imparting a natural strawberry flavor to food products, particularly in strawberry and other fruit-flavored items. Its strong aroma makes it an ideal choice for enhancing the taste and appeal of various foodstuffs.
Used in Perfume Industry:
In the perfume industry, (3R,4S)-3,4-bis (benzoyloxy) dihydro-2(3H)-Furanone is utilized as a fragrance component to add a fresh, fruity, and sweet scent to perfumes and other scented products. Its unique aroma profile contributes to the creation of complex and long-lasting fragrances.
Used in Cosmetic Industry:
(3R,4S)-3,4-bis (benzoyloxy) dihydro-2(3H)-Furanone is employed in the cosmetic industry as a scent ingredient to provide a pleasant and natural strawberry aroma to products such as lotions, creams, and other skincare items. Its incorporation enhances the sensory experience and consumer appeal of these cosmetics.
Synthesis:
(3R,4S)-3,4-bis (benzoyloxy) dihydro-2(3H)-Furanone is synthesized through the esterification of r-butyrolactone with benzoic anhydride, a process that results in the formation of this aromatic compound with a wide range of applications across different industries.

Upstream product

• 98-88-4 benzoyl chloride 
• 70753-61-6 calcium L-threonate 
• 21730-93-8 L-threonic acid-4-lactone 

Downstream Products

• 325683-79-2 1-(2',3'-di-O-benzoyl-α-L-threofuranosyl)thymine 
• 425394-07-6 N²,N⁶-dibenzoyl-9-(2',3'-di-O-benzoyl-α-L-threofuranosyl)-2,6-diaminopurine 
• 325683-81-6 N⁴-benzoyl-1-(2',3'-di-O-benzoyl-α-L-threofuranosyl)cytosine 
• 325683-77-0 1-O-acetyl-2,3-di-O-benzoyl-L-threofuranose 
• 537690-74-7 2,3-di-O-benzoyl-L-threofuranose 

Relevant articles and documents

Selective Prebiotic Synthesis of α-Threofuranosyl Cytidine by Photochemical Anomerization

The structure of life's first genetic polymer is a question of intense ongoing debate. The “RNA world theory” suggests RNA was life's first nucleic acid. However, ribonucleotides are complex chemical structures, and simpler nucleic acids, such as threose nucleic acid (TNA), can carry genetic information. In principle, nucleic acids like TNA could have played a vital role in the origins of life. The advent of any genetic polymer in life requires synthesis of its monomers. Here we demonstrate a high-yielding, stereo-, regio- and furanosyl-selective prebiotic synthesis of threo-cytidine 3, an essential component of TNA. Our synthesis uses key intermediates and reactions previously exploited in the prebiotic synthesis of the canonical pyrimidine ribonucleoside cytidine 1. Furthermore, we demonstrate that erythro-specific 2′,3′-cyclic phosphate synthesis provides a mechanism to photochemically select TNA cytidine. These results suggest that TNA may have coexisted with RNA during the emergence of life.

The α-L-Threofuranosyl-(3′ → 2′)-oligonucleotide system ('TNA'): Synthesis and pairing properties

Our studies of α-L-Threofuranosyl-(3′ → 2′)-oligonucleotides ('TNA') are part of a systematic experimental inquiry into the base-pairing properties of potentially natural nucleic acid alternatives taken from RNA's close structural neighborhood. TNA is an efficient Watson-Crick base-pairing system and has the capability of informational cross-pairing with both RNA and DNA. This property, together with the system's constitutional and (presumed) generational simplicity, warrants special scrutiny of TNA in the context of the search for chemical clues to RNA's origin.