Sugarcane derived semi-synthetic cosmetic ingredients, methods of production thereof, and personal care products derived therefrom
AssigneeAmyris, Inc.
InventorsGreg Oniel BUCHANAN, Anushree DAS, Lovedeep KAUR, Mikhail MOTORNOV, Daan Thorn LEESON, Punitha VEDANTHAM
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Abstract
The present invention provides compounds derived from farnesene and methods of producing the compounds from farnesene. In addition, compositions and methods of using the compositions as personal care products and other consumer products are provided, wherein the compositions comprise compounds derived from farnesene.
Claims68
A compound of Formula (II):
- wherein R1 is independently, at each occurrence, selected from H and
- or a salt and/or stereoisomer thereof.
Compound (I-C):
- or a salt and/or stereoisomer thereof.
A method of producing a compound of Formula (I):
- or a salt and/or stereoisomer thereof comprising contacting hexahydrofarnesoic acid:
- with R2OH and an acid;
- wherein R2 is selected from a straight or branched C1-6alkyl.
A method of producing a compound of Formula (I):
- or a salt and/or stereoisomer thereof comprising:
- converting hexahydrofarnesoic acid:
- to hexahydrofarnesyl chloride:
- isolating the hexahydrofarnesyl chloride;
- and
- contacting the hexahydrofarnesyl chloride with R2OH;
- wherein R2 is selected from a straight or branched C1-6alkyl.
A method of producing a compound of any one of claims I-4, comprising:
- contacting hexahydrofarnesoic acid:
- with ascorbic acid and a coupling agent.
A method of producing a compound of any one of claims I-4, comprising:
- converting hexahydrofarnesoic acid:
- to hexahydrofarnesyl chloride:
- isolating the hexahydrofarnesyl chloride;
- and
- contacting the hexahydrofarnesyl chloride with ascorbic acid and an organic base.
The method of any one of claims 6-34, further comprising producing the hexahydrofarnesoic acid via a process that comprises:
- contacting hexahydrofarnesol (HHF):
- with NaH2PO4, TEMPO, and bleach in the absence of solvent;
- and
- adding NaClO2 over a period between about 4.5 and 6.5 hours.
A method of producing hexahydrofarnesoic acid (HHFA):
- or a salt and/or stereoisomer thereof comprising:
- contacting hexahydrofarnesol (HHF):
- with NaH2PO4, TEMPO, and bleach in the absence of solvent;
- and
- adding NaClO2 over a period between about 4.5 and 6.5 hours.
A personal care product comprising a compound selected from
- Compound (I-A)
- Ethyl-hexahydrofarnesoate;
- Compound (I-B)
- Isopropyl-hexahydrofarnesoate;
- Compound (I-C)
- Hexahydrofarnesyl-hexahydrofarnesoate;
- Compound (II- A)
- Dihexahydrofarnesyl ascorbate;
- Compound (II- B)
- Trihexahydrofarnesyl ascorbate;
- Compound (II- C)
- Tetrahexahydrofarnesyl ascorbate;
- or a combination thereof.
Dependencies are inferred from the claim text.